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DE69636478T2 - BICYCLIC AMINO DERIVATIVES AND PGD2 ANTAGONISTS CONTAINING - Google Patents

BICYCLIC AMINO DERIVATIVES AND PGD2 ANTAGONISTS CONTAINING Download PDF

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Publication number
DE69636478T2
DE69636478T2 DE69636478T DE69636478T DE69636478T2 DE 69636478 T2 DE69636478 T2 DE 69636478T2 DE 69636478 T DE69636478 T DE 69636478T DE 69636478 T DE69636478 T DE 69636478T DE 69636478 T2 DE69636478 T2 DE 69636478T2
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meoh
mhz
alkyl
cdcl
hydrogen
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DE69636478T
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German (de)
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DE69636478D1 (en
Inventor
Mitsuaki Ohtani
Akinori Arimura
Tatsuo Tsuri
Junji Kishino
Tsunetoshi Honma
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Shionogi and Co Ltd
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Shionogi and Co Ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/81—Amides; Imides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/16—Amides, e.g. hydroxamic acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/557—Eicosanoids, e.g. leukotrienes or prostaglandins
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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    • A61P27/00—Drugs for disorders of the senses
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
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    • C07C233/45—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
    • C07C233/52—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a ring other than a six-membered aromatic ring
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    • C07C233/57—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of rings other than six-membered aromatic rings
    • C07C233/63—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of rings other than six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
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    • C07C233/67—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
    • C07C233/74—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a ring other than a six-membered aromatic ring
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    • C07C233/81—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
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    • C07C233/81—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
    • C07C233/82—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
    • C07C233/84—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom of a saturated carbon skeleton containing rings
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    • C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C235/18—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated having at least one of the singly-bound oxygen atoms further bound to a carbon atom of a six-membered aromatic ring, e.g. phenoxyacetamides
    • C07C235/22—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated having at least one of the singly-bound oxygen atoms further bound to a carbon atom of a six-membered aromatic ring, e.g. phenoxyacetamides having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a ring other than a six-membered aromatic ring
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    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/32—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
    • C07C235/36—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a ring other than a six-membered aromatic ring
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    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/42—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton
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    • C07—ORGANIC CHEMISTRY
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    • C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/42—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/44—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
    • C07C235/54—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a ring other than a six-membered aromatic ring
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    • C07C235/70—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/84—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton with the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a six-membered aromatic ring
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    • C07C237/28—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton
    • C07C237/38—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton having the nitrogen atom of the carboxamide group bound to a carbon atom of a ring other than a six-membered aromatic ring
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    • C07C237/28—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton
    • C07C237/42—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton having nitrogen atoms of amino groups bound to the carbon skeleton of the acid part, further acylated
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    • C07C245/00—Compounds containing chains of at least two nitrogen atoms with at least one nitrogen-to-nitrogen multiple bond
    • C07C245/02—Azo compounds, i.e. compounds having the free valencies of —N=N— groups attached to different atoms, e.g. diazohydroxides
    • C07C245/06—Azo compounds, i.e. compounds having the free valencies of —N=N— groups attached to different atoms, e.g. diazohydroxides with nitrogen atoms of azo groups bound to carbon atoms of six-membered aromatic rings
    • C07C245/08—Azo compounds, i.e. compounds having the free valencies of —N=N— groups attached to different atoms, e.g. diazohydroxides with nitrogen atoms of azo groups bound to carbon atoms of six-membered aromatic rings with the two nitrogen atoms of azo groups bound to carbon atoms of six-membered aromatic rings, e.g. azobenzene
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    • C07C251/32—Oximes
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    • C07C255/00—Carboxylic acid nitriles
    • C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C255/57—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and carboxyl groups, other than cyano groups, bound to the carbon skeleton
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    • C07C271/06—Esters of carbamic acids
    • C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
    • C07C271/24—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a ring other than a six-membered aromatic ring
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    • C07C275/42—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by carboxyl groups
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    • C07C281/00—Derivatives of carbonic acid containing functional groups covered by groups C07C269/00 - C07C279/00 in which at least one nitrogen atom of these functional groups is further bound to another nitrogen atom not being part of a nitro or nitroso group
    • C07C281/06—Compounds containing any of the groups, e.g. semicarbazides
    • C07C281/08—Compounds containing any of the groups, e.g. semicarbazides the other nitrogen atom being further doubly-bound to a carbon atom, e.g. semicarbazones
    • C07C281/14—Compounds containing any of the groups, e.g. semicarbazides the other nitrogen atom being further doubly-bound to a carbon atom, e.g. semicarbazones the carbon atom being further bound to a carbon atom of a six-membered aromatic ring
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    • C07C311/06—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atoms of the sulfonamide groups bound to hydrogen atoms or to acyclic carbon atoms to acyclic carbon atoms of hydrocarbon radicals substituted by carboxyl groups
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    • C07C311/12—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing rings
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    • C07C311/20—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a ring other than a six-membered aromatic ring
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    • C07C311/22—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms
    • C07C311/29—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
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    • C07C311/37—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
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    • C07C311/30—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups
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Abstract

A compound of the formula (I): <CHEM> wherein <CHEM> for example, a compound below: <CHEM> wherein R1 is CH3, H or Na; and X1-X2-X3 is <CHEM> or a salt or a hydrate thereof is useful as a PGD2 antagonist and can be used as a drug for treating diseases in which mast cell dysfunction is involved, for example, systemic mastocytosis and disorder of systemic mast cell activation, and also tracheal contraction, asthma, allergic rhinitis, allergic conjunctivitis, urticaria, injury due to ischemic reperfusion, and as an anti-inflammatory agent. It is particularly useful in the treatment of nasal occlusion.

Description

GEBIET DER ERFINDUNGFIELD OF THE INVENTION

Die vorliegende Erfindung betrifft bicyclische Aminoderivate und sie enthaltende Prostaglandin D2-Antagonisten (nachstehend als PDG2 bezeichnet).The present invention relates to bicyclic amino derivatives and prostaglandin D 2 antagonists containing them (hereinafter referred to as PDG 2 ).

HINDERGRUND DER ERFINDUNGBACKGROUND OF THE INVENTION

Es ist bekannt, dass einige bicyclische Aminoderivate als Thromboxan A2 (TXA2) Antagonisten (japanische Offenlegungsschrift Nr. JP63-139161) nützlich sind. Jedoch beschreibt die japanische Offenlegungsschrift Nr. JP63-139161 die Verbindungen nur als nützliche TXA2-Antagonisten und schlägt keinen Nutzen dieser als PGD2-Antagonisten vor.It is known that some bicyclic amino derivatives are useful as thromboxane A 2 (TXA 2 ) antagonists (Japanese Patent Laid-Open No. JP63-139161). However, Japanese Patent Laid-Open Publication No. JP63-139161 describes the compounds as useful TXA 2 antagonists only and suggests no benefit thereof as PGD 2 antagonists.

Es ist nämlich bekannt, dass TXA2 Aktivitäten wie eine Wirkung gegen Plättchenagglutination, Thrombogenese u.s.w. aufweist. Es wird deshalb in Erwägung gezogen, dass der TXA2-Antagonist als Antithrombotikum und auch bei der Behandlung von Herzinfarkt oder Asthma durch Entgegenwirken von TXA2 nützlich ist.Namely, it is known that TXA 2 has activities such as platelet agglutination, thrombogenesis, etc. It is therefore contemplated that the TXA 2 antagonist is useful as an antithrombotic and also in the treatment of myocardial infarction or asthma by counteracting TXA 2 .

EP-A-608 847 offenbart carbocyclische Sulfonamide als Agonisten oder Antagonisten von PGEZ.EP-A-608 847 discloses carbocyclic sulfonamides as agonists or antagonists from PGEZ.

EP-A-312 906 offenbart Sulfonamidderivate, welche als TXA2-Antagonisten verwendet werden können.EP-A-312 906 discloses sulfonamide derivatives which can be used as TXA 2 antagonists.

EP-A-0 226 346 offenbart bicyclische Sulfonamidderivate, welche als antithrombotische, antivasokonstriktorische und antibronchokonstriktorische Arzneistoffe verwendet werden können.EP-A-0 No. 226,346 discloses bicyclic sulfonamide derivatives useful as antithrombotic, antivasoconstrictive and antibronchoconstrictive drugs can be used.

EP-A-0 150 709 offenbart 7-Oxabicycloheptanprostaglandin-Analoge als Herz-Kreislauf-Mittel, welche bei der Behandlung einer thrombolytischen Krankheit nützlich sind.EP-A-0 150,709 discloses 7-oxabicycloheptane prostaglandin analogs as cardiovascular agents, which are useful in the treatment of a thrombolytic disease.

EP-A-0290285 offenbart bicyclische Sulfonamidderivate und deren Verwendung bei der Behandlung von Krankheiten wie Angina pectoris, Herzinfarkt und Hirninfarkt.EP-A-0290285 discloses bicyclic sulfonamide derivatives and their use in the treatment of diseases such as angina, myocardial infarction and cerebral infarction.

Ein TXA2-Rezeptorantagonist, „S-1452", wird in Int. Arc. Allergy Immunol. (1992) 98, 239–246, Arimura et al., „Antiasthmatic Activity of a Novel Thromboxane A2 Antagonist, S-1452, in Guinea Pigs" ( XP 00 291 6327 ) offenbart.A TXA 2 receptor antagonist, "S-1452", is described in Int. Arc. Allergy Immunol. (1992) 98, 239-246, Arimura et al., "Antiasthmatic Activity of a Novel Thromboxane A 2 Antagonist, S-1452," in Guinea Pigs "( XP 00 291 6327 ) disclosed.

Andererseits ist der PGD2-Antagonist der vorliegenden Erfindung bei der Verbesserung von Zuständen aufgrund einer übermäßigen Produktion von PGD2 nützlich. Speziell ist er als ein Arzneistoff zur Behandlung von Krankheiten nützlich, in welchen eine Fehlfunktion der Mastzellen beteiligt ist, zum Beispiel systemischer Mastozytose und Störung der systemischen Mastzellaktivierung und auch trachealer Kontraktion, Asthma, allergischer Rhinitis, allergischer Konjunktivitis, Urtikaria, Verletzungen aufgrund von Ischämie-Reperfusion und Entzündung.On the other hand, the PGD 2 antagonist of the present invention is useful in improving conditions due to excessive production of PGD 2 . Specifically, it is useful as a drug for the treatment of diseases involving mast cell dysfunction, for example, systemic mastocytosis and disorder of systemic mast cell activation and also tracheal contraction, asthma, allergic rhinitis, allergic conjunctivitis, urticaria, injuries due to ischemia. Reperfusion and inflammation.

Wie aus dem Vorstehenden ersichtlich, sind der TXA2-Antagonist und der PGD2-Antagonist voneinander vollständig verschieden, was die aktive Stelle (active site), Wirkmechanismus und Anwendung betrifft und weisen völlig verschiedene Charakteristika auf. Demgemäß ist nie angenommen worden, dass irgendeine Verbindung diese Aktivitäten gleichzeitig aufweisen könnte.As seen from the above, the TXA 2 antagonist and the PGD 2 antagonist are completely different from each other in terms of the active site, mechanism of action and application and have completely different characteristics. Accordingly, it has never been assumed that any compound could simultaneously exhibit these activities.

PGD2 wird durch PGG2 und PGH2 aus Arachidonsäure durch die Wirkung von Cyclooxygenase, die durch immunologische oder nicht-immunologische Stimulierung aktiviert wird, hergestellt und ist das bedeutendste Prostanoid, das von Mastzellen hergestellt und freigesetzt wird. PGD2 weist verschiedene, starke physiologische und pathologische Aktivitäten auf. Zum Beispiel kann PGD2 eine kräftige tracheale Kontraktion verursachen, welche zu Bronchialasthma führt und in einem systemischen allergischen Zustand kann es die periphären Gefäße erweitern, welches zu einem anaphylaktischen Schock führt. Insbesondere ist der Idee viel Aufmerksamkeit geschenkt worden, dass PGD2 eine der kausalen Substanzen ist, die für den Ausbruch einer Nasenokklusion bei allergischer Rhinitis verantwortlich ist. Deshalb ist vorgeschlagen worden, einen Inhibitor der PGD2-Biosynthese oder einen Antagonisten des PGD2-Rezeptors als einen Arzneistoff zur Verringerung der Nasenokklusion zu entwickeln. Möglicherweise beeinflusst jedoch der Inhibitor der PGD2-Biosynthese die Prostaglandinsynthesen in anderen Organismen beträchtlich, und es ist deshalb wünschenswert, einen Antagonisten (Blocker) spezifisch auf den PGD2-Rezeptor zu entwickeln.PGD 2 is produced by PGG 2 and PGH 2 from arachidonic acid by the action of cyclooxygenase activated by immunological or non-immunological stimulation and is the most important prostanoid produced and released by mast cells. PGD 2 has various strong physiological and pathological activities. For example, PGD 2 may cause a strong tracheal contraction leading to bronchial asthma, and in a systemic allergic condition, it may dilate the peripheral vessels leading to anaphylactic shock. In particular, much attention has been given to the idea that PGD 2 is one of the causal substances responsible for the onset of nasal occlusion in allergic rhinitis. Therefore, it has been proposed to develop an inhibitor of PGD 2 biosynthesis or an antagonist of the PGD 2 receptor as a drug for reducing nasal occlusion. However, the inhibitor of PGD 2 biosynthesis may significantly affect prostaglandin syntheses in other organisms, and it is therefore desirable to specifically develop an antagonist (blocker) to the PGD 2 receptor.

OFFENBARUNG DER ERFINDUNGDISCLOSURE OF THE INVENTION

Die hier genannten Erfinder haben gründlich geforscht, um PGD2-Rezeptorantagonisten (Blocker) spezifisch auf den PGD2-Rezeptor zu entwickeln und stellten fest, dass Verbindungen der nachstehenden Formel (Ib) oder ihre Salze eine starke Aktivität als PGD2-Rezeptorantagonisten aufweisen und chemisch und biochemisch stabil sind.The present inventors have conducted extensive research to specifically develop PGD 2 receptor antagonists (blockers) on the PGD 2 receptor and found that compounds of the following formula (Ib) or their salts have strong activity as PGD 2 receptor antagonists, and are chemically and biochemically stable.

Demgemäß stellt die vorliegende Erfindung einen PGD2-Antagonisten bereit, welcher eine Verbindung der Formel (Ib) umfasst:

Figure 00030001
steht,
wobei A Alkylen ist, das gegebenenfalls durch ein Heteroatom oder Phenylen unterbrochen sein kann, eine Oxogruppe enthält und/oder eine ungesättigte Bindung aufweist;
B Wasserstoff, Alkyl, Aralkyl oder Acyl ist;
R für COOR1, CH2OR2 oder CON(R3)R4 steht;
R1 Wasserstoff oder Alkyl ist;
R2 Wasserstoff oder Alkyl ist;
R3 und R4 jeweils unabhängig Wasserstoff, Alkyl, Hydroxy oder Alkylsulfonyl sind;
X1 eine Einfachbindung, Phenylen, Naphthylen, Thiophendiyl, Indoldiyl oder Oxazoldiyl ist;
X2 eine Einfachbindung, -N=N-, -N=CH-, -CH=N-, -CH=N-N-, -CH=N-O-, -C=NNHCSNH-, -C=NNHCONH-, -CH=CH-, -CH(OH)-, -C(Cl)=C(Cl)-, -(CH2)n-, Ethinylen, -N(R5)-, -N(R51)CO-, -N(R52)SO2-, -N(R53)CON(R54)-, -CON(R55)-, -SO2N(R56)-, -O-, -S-, -SO-, -SO2-, -CO-, Oxadiazoldiyl, Thiadiazoldiyl oder Tetrazoldiyl ist;
X3 Alkyl, Alkenyl, Alkinyl, Aryl, Aralkyl, ein heterocyclischer Rest, Cycloalkyl, Cycloalkenyl, Thiazolinylidenmethyl, Thiazolidinylidenmethyl, -CH=NR6 oder -N=C(R7)R8 ist;
R5, R51, R52, R53, R54, R55 und R56 jeweils Wasserstoff oder Alkyl sind;
R6 Wasserstoff, Alkyl, Hydroxy, Alkoxy, Carbamoyloxy, Thiocarbamoyloxy, Ureido oder Thioureido ist;
R7 und R8 jeweils unabhängig Alkyl, Alkoxy oder Aryl sind;
und n gleich 1 oder 2 ist;
wobei ein cyclischer Substituent einen bis drei Substituenten, ausgewählt aus Nitro, Alkoxy, Sulfamoyl, substituiertem oder unsubstituiertem Amino, Acyl, Acyloxy, Hydroxy, Halogen, Alkyl, Alkinyl, Carboxy, Alkoxycarbonyl, Aralkoxycarbonyl, Aryloxycarbonyl, Mesyloxy, Cyano, Alkenyloxy, Hydroxyalkyl, Trifluormethyl, Alkylthio, -N=PPh3, Oxo, Thioxo, Hydroxyimino, Alkoxyimino, Phenyl und Alkylendioxy oder deren Salzen oder Hydraten davon, aufweisen kann; mit der Maßgabe, dass die Verbindungen (a), wobei X1 und X2 Einfachbindungen sind und X3 Phenyl ist; (b), wobei X1 eine Einfachbindung ist, X2 für -O- steht und X3 Benzyl ist;
Figure 00040001
ausgenommen sind.Accordingly, the present invention provides a PGD 2 antagonist comprising a compound of formula (Ib):
Figure 00030001
stands,
wherein A is alkylene, which may optionally be interrupted by a heteroatom or phenylene, contains an oxo group and / or has an unsaturated bond;
B is hydrogen, alkyl, aralkyl or acyl;
R is COOR 1 , CH 2 OR 2 or CON (R 3 ) R 4 ;
R 1 is hydrogen or alkyl;
R 2 is hydrogen or alkyl;
R 3 and R 4 are each independently hydrogen, alkyl, hydroxy or alkylsulfonyl;
X 1 is a single bond, phenylene, naphthylene, thiophenediyl, indolediyl or oxazolediyl;
X 2 is a single bond, -N = N-, -N = CH-, -CH = N-, -CH = NN-, -CH = NO-, -C = NNHCSNH-, -C = NNHCONH-, -CH = CH, -CH (OH) -, -C (Cl) CC (Cl) -, - (CH 2 ) n -, ethynylene, -N (R 5 ) -, -N (R 51 ) CO-, - N (R 52) SO 2 -, -N (R 53) CON (R 54) -, -CON (R 55) -, -SO 2 N (R 56) -, -O-, -S-, -SO Is -SO 2 -, -CO-, oxadiazolediyl, thiadiazolediyl or tetrazolediyl;
X 3 is alkyl, alkenyl, alkynyl, aryl, aralkyl, heterocyclic, cycloalkyl, cycloalkenyl, thiazolinylidenemethyl, thiazolidinylidenemethyl, -CH = NR 6 or -N = C (R 7 ) R 8 ;
R 5 , R 51 , R 52 , R 53 , R 54 , R 55 and R 56 are each hydrogen or alkyl;
R 6 is hydrogen, alkyl, hydroxy, alkoxy, carbamoyloxy, thiocarbamoyloxy, ureido or thioureido;
R 7 and R 8 are each independently alkyl, alkoxy or aryl;
and n is 1 or 2;
wherein a cyclic substituent has one to three substituents selected from nitro, alkoxy, sulfamoyl, substituted or unsubstituted amino, acyl, acyloxy, hydroxy, halogen, alkyl, alkynyl, carboxy, alkoxycarbonyl, aralkoxycarbonyl, aryloxycarbonyl, mesyloxy, cyano, alkenyloxy, hydroxyalkyl, Trifluoromethyl, alkylthio, -N = PPh 3 , oxo, thioxo, hydroxyimino, alkoxyimino, phenyl and alkylenedioxy or their salts or hydrates thereof; with the proviso that the compounds are (a) wherein X 1 and X 2 are single bonds and X 3 is phenyl; (b) wherein X 1 is a single bond, X 2 is -O- and X 3 is benzyl;
Figure 00040001
with exception of.

Die Verbindungen der Formeln:

Figure 00050001
sind von dem Bereich des Anspruchs 1 dieser/dieses Anmeldung/Patents mittels Disclaimer ausgenommen, welche nach Hinterlegung der Anmeldung in die Beschreibung aufgenommen wurden. Eine oder mehrere dieser Verbindungen erscheinen jeweils in EP-A-226 346, EP-A-290 285 und Chem. Pharm. Bull. 37 (6), 1524–1533, K. Seno, S. Hagishita, „Thromboxane A2 Receptor Antagonists III. Synthesis and Pharmacological Activity of 6,6-Dimethylbicyclo[3.1.1]heptane Derivatives with a Substituted Sulfonylamino Group C-2" XP2058537 . Diese Verbindungen sind als zufällige Vorwegnahmen gemäß den Entscheidungen G1/03 und G2/03 mittels Disclaimer ausgeschlossen worden.The compounds of the formulas:
Figure 00050001
are excluded from the scope of claim 1 of this application / patent by means of a disclaimer which has been included in the description after filing the application. One or more of these compounds appear in EP-A-226 346, EP-A-290 285 and Chem. Pharm. Bull. 37 (6), 1524-1533, K. Seno, S. Hagishita, "Thromboxane A 2 Receptor Antagonists III. Synthesis and Pharmacological Activity of 6,6-Dimethylbicyclo [3.1.1] Heptane Derivatives with a Substituted Sulfonylamino Group C-2 XP2058537 , These connections have been excluded as accidental anticipations according to the decisions G1 / 03 and G2 / 03 by means of a disclaimer.

Beispiele für stärker bevorzugte Verbindungen schließen jene der Formel (Ib) ein, wobei R für COOR1 (R1 ist wie vorstehend definiert) steht oder ein Salz oder Hydrat davon.Examples of more preferred compounds include those of formula (Ib) wherein R is COOR 1 (R 1 is as defined above) or a salt or hydrate thereof.

Ebenso schließen Beispiele für Verbindungen der vorliegenden Erfindung jene der Formel (Ib) ein, wobei X1 ein Phenylen oder Thiophendiyl ist, X2 eine Einfachbindung, -N-N-, -CH=CH-, Ethinylen, -O-, -S-, -CO-, -CON(R55)- (R55 ist wie vorstehend definiert), -N(R51)CO- (R51 ist wie vorstehend definiert) ist und X3 Phenyl ist, oder ein Salz oder Hydrat davon.Also, examples of compounds of the present invention include those of formula (Ib) wherein X 1 is a phenylene or thiophenediyl, X 2 is a single bond, -NN-, -CH = CH-, ethynylene, -O-, -S-, -CO-, -CON (R 55 ) - (R 55 is as defined above), -N (R 51 ) CO- (R 51 is as defined above) and X 3 is phenyl, or a salt or hydrate thereof.

Beispiele für stärker bevorzugte Ausführungsformen schließen jene ein, in welchen B Wasserstoff ist, X1 und X2 beide eine Einfachbindung sind, X3 Thienyl, Thiazolyl, Thiadiazolyl, Isothiazolyl, Pyrrolyl, Pyridyl, Benzofuryl, Benzimidazolyl, Benzothienyl, Dibenzofuryl, Dibenzothienyl, Chinolyl oder Indolyl ist oder ein Salz oder Hydrat davon. Ebenso schließen Beispiele jene ein, in welchen X1 Phenylen, Thiophendiyl, Indoldiyl oder Oxazoldiyl ist, X2 eine Einfachbindung, -N=N-, Ethinylen, -S- oder -O- ist, und X3 Aryl oder ein heterocyclischer Rest ist oder ein Salz oder Hydrat davon.Examples of more preferred embodiments include those in which B is hydrogen, X 1 and X 2 are both a single bond, X 3 is thienyl, thiazolyl, thiadiazolyl, isothiazolyl, pyrrolyl, pyridyl, benzofuryl, benzimidazolyl, benzothienyl, dibenzofuryl, dibenzothienyl, quinolyl or indolyl or a salt or hydrate thereof. Also, examples include those in which X 1 is phenylene, thiophenediyl, indolediyl or oxazolediyl, X 2 is a single bond, -N = N-, ethynylene, -S- or -O-, and X 3 is aryl or a heterocyclic radical or a salt or hydrate thereof.

Die Verbindungen der allgemeinen Formel (Ib) sind neue Verbindungen, die durch die hier genannten Erfinder synthetisiert wurden.The Compounds of general formula (Ib) are new compounds, which were synthesized by the present inventors.

Die in der ganzen vorliegenden Beschreibung verwendeten Begriffe sind wie nachstehend definiert.The are terms used throughout the present specification as defined below.

Der Begriff „Alkylen" bedeutet eine gerade oder verzeigte C1-C9-Alkylenkette, zum Beispiel Methylen, Methylmethylen, Dimethylmethylen, Methylethylmethylen, Ethylen, Trimethylen, Tetramethylen, Pentamethylen, Hexamethylen, Heptamethylen, Octamethylen, Nonamethylen oder dergleichen. Das vorstehende Alkylen kann durch ein Heteroatom(e) (Sauerstoff, Schwefel, Stickstoffatom oder dergleichen) oder Phenylen (z.B. 1,4-Phenylen, 1,3-Phenylen, 1,2-Phenylen oder dergleichen), das einen oxo-Rest enthält und/oder eine oder mehrere Doppel- oder Dreifachbindungen an jeder beliebigen Position in der Kette aufweist, unterbrochen sein. Beispiele schließen -(CH2)2-O-CH2-, -(CH2)2-O-(CH2)2-, -(CH2)2-O-(CH2)3-, -(CH2)2-O-(CH2)2-, -(CH2)2-O-(CH2)5-, -(CH2)2-O-(CH2)6-, -(CH2)2-S-(CH2)2-, -(CH2)3-S-(CH2)2-, -CH2-S-CH2-, -CH2-S-(CH2)4-, -CH2-N(CH3)-CH2-, -CH2-NH-(CH2)2-, -(CH2)2-N(CH2CH3)-(CH2)3-, -(CH2)2-1,4-Phenylen-CH2-, -(CH2)2-O-1,3-Phenylen-CH2-, -(CH2)2-O-1,2-Phenylen-CH2-, -(CH2)2-O-1,4-Phenylen-CH2-, -CH=CH-S-CH2-1,4-Phenylen-CH2-, -CH=CH-S-1,3-Phenylen-(CH2)2-, 2-Oxopropylen, 3-Oxopentylen, 5-Oxohexylen, Vinylen, 1-Propenylen, 2-Propenylen, 1-Butenylen, 2-Butenylen, 3-Butenylen, 1,2-Butadienylen, 1,3-Butadienylen, 1-Pentenylen, 2-Pentenylen, 3-Pentenylen, 4-Pentenylen, 1,2-Pentadienylen, 1,3-Pentadienylen, 1,4-Pentadienylen, 2,3-Pentadienylen, 2,4-Pentadienylen, 1-Hexenylen, 2-Hexenylen, 3-Hexenylen, 4-Hexenylen, 5-Hexenylen, 1,2-Hexadienylen, 1,3-Hexadienylen 1,4-Hexadienylen, 1,5-Hexadienylen, 2,3-Hexadienylen, 2,4-Hexadienylen 2,5-Hexadienylen, 3,4-Hexadienylen, 3,5-Hexadienylen, 4,5-Hexadienylen, 1,1-Dimethyl-4-hexenylen, 1-Heptenylen, 2-Heptenylen, 3-Heptenylen, 4-Heptenylen, 5-Heptenylen, 2,2-Dimethyl-5-heptenylen, 6-Heptenylen, 1,2-Heptadienylen, 1,3-Heptadienylen, 1,4-Heptadienylen, 1,5-Heptadienylen, 1,6-Heptadienylen, 2,3-Heptadienylen, 2,4-Heptadienylen, 2,5-Heptadienylen, 2,6-Heptadienylen, 3,4-Heptadienylen, 3,5-Heptadienylen, 3,6-Heptadienylen, 4,5-Heptadienylen, 4,6-Heptadienylen oder 5,6-Heptadienylen, 1-Propinylen, 3-Butinylen, 2-Pentinylen, 5-Hexinylen, 6-Heptinylen, -(CH2)-CH=CH-O-(CH2)2-, -CH2-S-(CH2)3-, -CH2-cis-CH=CH-1,2-Phenylen-CH2-, -CH=CH-1,4-Phenylen-(CH2)2-, -4-Oxo-4,5-hexenylen- und dergleichen ein.The term "alkylene" means a straight or branched C 1 -C 9 alkylene chain, for example, methylene, methylmethylene, dimethylmethylene, methylethylmethylene, ethylene, trimethylene, tetramethylene, pentamethylene, hexamethylene, heptamethylene, octamethylene, nonamethylene, or the like by a hetero atom (s) (oxygen, sulfur, nitrogen atom or the like) or phenylene (eg 1,4-phenylene, 1,3-phenylene, 1,2-phenylene or the like) containing an oxo radical and / or a or more double or triple bonds at any position in the chain, examples include - (CH 2 ) 2 -O-CH 2 -, - (CH 2 ) 2 -O- (CH 2 ) 2 -, - (CH 2 ) 2 -O- (CH 2 ) 3 -, - (CH 2 ) 2 -O- (CH 2 ) 2 -, - (CH 2 ) 2 -O- (CH 2 ) 5 -, - (CH 2 ) 2 -O- (CH 2 ) 6 -, - (CH 2 ) 2 -S- (CH 2 ) 2 -, - (CH 2 ) 3 -S- (CH 2 ) 2 -, -CH 2 -S -CH 2 -, -CH 2 -S- (CH 2 ) 4 -, -CH 2 -N (CH 3 ) -CH 2 -, -CH 2 -NH- (CH 2 ) 2 -, - (CH 2 ) 2 -N (CH 2 CH 3 ) - (CH 2 ) 3 -, - (CH 2 ) 2 -1,4-phenylene-CH 2 -, - (CH 2 ) 2 -O-1,3-phenylene-CH 2 -, - (CH 2 ) 2 -O-1,2-phenylene-CH 2 -, - (CH 2 ) 2 -O-1,4-phenylene-CH 2 -, -CH = CH-S-CH 2 -1,4-phenylene-CH 2 -, -CH = CH-S-1,3-phenylene - (CH 2 ) 2 -, 2-oxopropylene, 3-oxopentylene, 5-oxohexylene, vinylene, 1-propenylene, 2-propenylene, 1-butenylene, 2-butenylene, 3-butenylene, 1,2-butadienylene, 1, 3-butadienylene, 1-pentenylene, 2-pentenylene, 3-pentenylene, 4-pentenylene, 1,2-pentadienylene, 1,3-pentadienylene, 1,4-pentadienylene, 2,3-pentadienylene, 2,4-pentadienylene, 1-hexenylene, 2-hexenylene, 3-hexenylene, 4-hexenylene, 5-hexenylene, 1,2-hexadienylene, 1,3-hexadienylene, 1,4-hexadienylene, 1,5-hexadienylene, 2,3-hexadienylene, 2 , 4-hexadienylene 2,5-hexadienylene, 3,4-hexadienylene, 3,5-hexadienylene, 4,5-hexadienylene, 1,1-dimethyl-4-hexenylene, 1-heptenylene, 2-heptenylene, 3-heptenylene, 4-heptenylene, 5-heptenylene, 2,2-dimethyl-5-heptenylene, 6-heptenylene, 1,2-heptadienylene, 1,3-heptadienylene, 1,4-heptadienylene, 1,5-heptadienylene, 1,6- Heptadienylene, 2,3-heptadienylene, 2 , 4-heptadienylene, 2,5-heptadienylene, 2,6-heptadienylene, 3,4-heptadienylene, 3,5-heptadienylene, 3,6-heptadienylene, 4,5-heptadienylene, 4,6-heptadienylene or 5,6 Heptadienylen, 1-propynylene, 3-butynylene, 2-pentynylene, 5-hexynylene, 6-heptinylene, - (CH 2 ) -CH = CH-O- (CH 2 ) 2 -, -CH 2 -S- (CH 2 ) 3 -, -CH 2 -cis-CH = CH-1,2-phenylene-CH 2 -, -CH = CH-1,4-phenylene- (CH 2 ) 2 -, -4-oxo-4, 5-hexenylene and the like.

Der Begriff „Alkyl" bedeutet eine gerade oder verzeigte C1-C20-Alkylkette, zum Beispiel Methyl, Ethyl, n-Propyl, i-Propyl, n-Butyl, i-Butyl, s-Butyl, t-Butyl, n-Pentyl, i-Pentyl, Neopentyl, t-Pentyl, Hexyl, Heptyl, Octyl, Nonyl, Decyl, Undecyl, Dodecyl, Tridecyl, Tetradecyl, Pentadecyl, Hexadecyl, Heptadecyl, Octadecyl, Nonadecyl, Icosyl und dergleichen.The term "alkyl" denotes a straight or branched C 1 -C 20 -alkyl chain, for example methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-butyl Pentyl, i-pentyl, neopentyl, t-pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, icosyl and the like.

Der Begriff „Aryl" bedeutet einen monocyclischen oder kondensierten C6-C14 Ring, zum Beispiel Phenyl, Naphthyl (z.B. 1-Naphthyl, 2-Naphthyl), Anthryl (z.B. 1-Anthryl, 2-Anthryl, 9-Anthryl), Phenanthryl (z.B. 2-Phenanthryl, 3-Phenanthryl, 9-Phenanthryl), Fluorenyl (z.B. 2-Fluorenyl) und dergleichen. Phenyl wird besonders bevorzugt.The term "aryl" means a monocyclic or fused C 6 -C 14 ring, for example phenyl, naphthyl (eg 1-naphthyl, 2-naphthyl), anthryl (eg 1-anthryl, 2-anthryl, 9-anthryl), phenanthryl (eg, 2-phenanthryl, 3-phenanthryl, 9-phenanthryl), fluorenyl (eg, 2-fluorenyl), and the like, phenyl is particularly preferred.

Der Begriff „Aralkyl" bedeutet einen Rest, der durch Substitution eines wie vorstehend definierten Alkyls mit einem vorstehenden Aryl an jeder geeigneten Position an dem Alkyl gebildet wird. Beispiele schließen Benzyl, Phenethyl, Phenylpropyl (z.B. 3-Phenylpropyl), Naphthylmethyl (z.B. α-Naphthylmethyl), Anthrylmethyl (z.B. 9-Anthrylmethyl), Phenanthrylmethyl (z.B. 3-Phenanthrylmethyl) und dergleichen ein.Of the Term "aralkyl" means a radical, by substitution of an alkyl as defined above a protruding aryl at any suitable position on the alkyl is formed. Examples include benzyl, Phenethyl, phenylpropyl (e.g., 3-phenylpropyl), naphthylmethyl (e.g., α-naphthylmethyl), Anthrylmethyl (e.g., 9-anthrylmethyl), phenanthrylmethyl (e.g., 3-phenanthrylmethyl) and the like.

Der Begriff „Acyl" bedeutet C1-C9 Acyl, das sich von einer aliphatischen Carbonsäure, zum Beispiel Ameisen-, Essig-, Propionyl-, Butyryl-, Valerylsäure und dergleichen ableitet.The term "acyl" means C 1 -C 9 acyl derived from an aliphatic carboxylic acid, for example formic, acetic, propionyl, butyryl, valeric acid and the like.

Der Begriff „Alkylsulfonyl" bedeutet einen Rest, der durch Substitution eines Sulfonyls mit einem vorstehenden Alkyl gebildet wird, zum Beispiel Methylsulfonyl, Ethylsulfonyl, Propylsulfonyl und dergleichen.Of the Term "alkylsulfonyl" means a radical, by substitution of a sulfonyl with an above alkyl is formed, for example, methylsulfonyl, ethylsulfonyl, propylsulfonyl and the same.

Der Begriff „Alkenyl" steht für eine gerade oder verzeigte C2-C20-Alkenylkette, welche einem vorstehenden Alkyl entspricht, das eine oder mehrere Doppelbindungen enthält. Beispiele schließen Vinyl, 1-Propenyl, 2-Propenyl, 1-Butenyl, 2-Butenyl, 3-Butenyl, 1,2-Butadienyl, 1-Pentenyl, 1,2-Pentadienyl, 2-Hexyenyl, 1,2-Hexadienyl, 3-Heptenyl, 1,5-Heptadienyl und dergleichen ein.The term "alkenyl" means a straight or branched C 2 -C 20 alkenyl chain which is a first corresponding alkyl containing one or more double bonds. Examples include vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1,2-butadienyl, 1-pentenyl, 1,2-pentadienyl, 2-hexyenyl, 1,2-hexadienyl, 3-heptenyl, 1,5-heptadienyl and the like.

Der Begriff „Alkinyl" ist eine gerade oder verzeigte C2-C20-Alkinylkette, welche einem vorstehenden Alkyl entspricht, das eine oder mehrere Dreifachbindungen enthält. Beispiele schließen Ethinyl, 1-Propinyl, 2-Propinyl, 1-Butinyl, 2-Butinyl, 3-Butinyl und dergleichen ein.The term "alkynyl" is a straight or branched C 2 -C 20 alkynyl chain which corresponds to an above alkyl containing one or more triple bonds, examples being ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl , 3-butynyl and the like.

Der Begriff „heterocyclischer Rest" bedeutet einen 5–7-gliedrigen cyclischen Rest, der ein oder mehrere Heteroatome, unabhängig ausgewählt aus einem Sauerstoff, Schwefel- und/oder Stickstoffatom in dem Ring enthält und gegebenenfalls mit einem Kohlenstoffring oder einem anderen heterocyclischen Rest an jeder geeigneten Position kondensiert ist. Beispiele schließen Pyrrolyl (z.B. 1-Pyrrolyl, 3-Pyrrolyl), Indolyl (z.B. 2-Indolyl, 3-Indolyl, 6-Indolyl), Carbazolyl (z.B. 2-Carbazolyl, 3-Carbazolyl), Imidazolyl (z.B. 1-Imidazolyl, 4-Imidazolyl), Pyrazolyl (z.B. 1-Pyrazolyl, 3-Pyrazolyl), Benzimidazolyl (z.B. 2-Benzimidazolyl, 5-Benzimidazolyl), Indazolyl (z.B. 3-Indazolyl), Indolizinyl (z.B. 6-Indolizinyl), Pyridyl (z.B. 2-Pyridyl, 3-Pyridyl, 4-Pyridyl), Chinolyl (z.B. 8-Chinolyl), Isochinolyl (z.B. 3-Isochinolyl), Acridyl (z.B. 1-Acridyl), Phenanthrydinyl (z.B. 2-Phenanthrydinyl, 3-Phenanthrydinyl), Pyridazinyl (z.B. 3-Pyridazinyl), Pyrimidinyl (z.B. 4-Pyrimidinyl), Pyrazinyl (z.B. 2-Pyrazinyl), Cinnolinyl (z.B. 3-Cinnolinyl), Phthaladinyl (z.B. 5-Phthaladinyl), Chinazolinyl (z.B. 2-Chinazolinyl), Isoxazolyl (z.B. 3-Isoxazolyl, 4-Isoxazolyl), Benzisoxazolyl (z.B. 1,2-Benzisoxazol-4-yl, 2,1-Benzisoxazol-3-yl), Oxazolyl (z.B. 2-Oxazolyl, 4-Oxazolyl, 5-Oxazolyl), Benzoxazolyl (z.B. 2-Benzoxazolyl), Benzoxadiazolyl (z.B. 4-Benzoxadiazolyl), Isothiazolyl (z.B. 3-Isothiazolyl, 4-Isothiazolyl) Benzisothiazolyl (z.B. 1,2-Benzisothiazol-3-yl, 2,1-Benzisothizol-5-yl), Thiazolyl (z.B. 2-Thiazolyl), Benzothiazolyl (z.B. 2-Benzothiazolyl), Thiadiazolyl (z.B. 1,2,3-Thiadiazol-4-yl), Oxadiazolyl (z.B. 1,3,4-Oxadiazol-2-yl), Dihydroxadiazolyl (z.B. 4,5-Dihydro-1,2,4-oxadiazol-3-yl), Furyl (z.B. 2-Furyl, 3-Furyl), Benzofuryl (z.B. 3-Benzofuryl), Isobenzofuryl (z.B. 1-Isobenzofuryl), Thienyl (z.B. 2-Thienyl, 3-Thienyl), Benzothienyl (1-Benzothiophen-2-yl, 2-Benzothiophen-1-yl), Tetrazolyl (z.B. 5-Tetrazolyl), Benzodioxolyl (z.B. 1,3-Benzodioxol-5-yl), Dibenzofuryl (z.B. 2-Dibenzofuryl, 3-Dibenzofuryl), Dibenzoxepinyl (z.B. Dibenz[b,f]oxepin-2-yl), Dihydrodibenzoxepinyl (z.B. Dihydrodibenz[b,f]oxepin-2-yl, Chromenyl (z.B. 2H-Chromen-3-yl, 4H-Chromen-2-yl), Dibenzothiepinyl (z.B. Dibenzo[b,f]thiepin-3-yl, Dihydrodibenzo[b,f]thiepin-3-yl), Morpholinyl (z.B. 1,4-Morpholin-4-yl), Phenothiadinyl (2-Phenothiadinyl), Cyclopentathienyl (z.B. Cyclopenta[b]thiophen-3-yl), Cyclohexathienyl (z.B. Cyclohexa[b]thiophen-3-yl), Cycloheptathienyl (z.B. Cyclohepta[b]thiophen-3-yl), Dibenzothienyl (z.B. 2-Dibenzothienyl), Dibenzopyranyl (z.B. 2-Dibenzopyranyl), Dibenzo-p-dioxyl (z.B. 2-Dibenzo-p-dioxyl) und dergleichen ein.Of the Term "heterocyclic Rest "means one 5-7 membered cyclic radical containing one or more heteroatoms, independently selected from an oxygen, sulfur and / or nitrogen atom in the ring contains and optionally with a carbon ring or another heterocyclic radical is condensed at any suitable position. Close examples Pyrrolyl (e.g., 1-pyrrolyl, 3-pyrrolyl), indolyl (e.g., 2-indolyl, 3-indolyl, 6-indolyl), carbazolyl (e.g., 2-carbazolyl, 3-carbazolyl), Imidazolyl (e.g., 1-imidazolyl, 4-imidazolyl), pyrazolyl (e.g., 1-pyrazolyl, 3-pyrazolyl), Benzimidazolyl (e.g., 2-benzimidazolyl, 5-benzimidazolyl), indazolyl (e.g., 3-indazolyl), indolizinyl (e.g., 6-indolizinyl), pyridyl (e.g. 2-pyridyl, 3-pyridyl, 4-pyridyl), quinolyl (e.g., 8-quinolyl), isoquinolyl (e.g., 3-isoquinolyl), acridyl (e.g., 1-acridyl), phenanthrydinyl (e.g., 2-phenanthrydinyl, 3-phenanthrydinyl), pyridazinyl (e.g., 3-pyridazinyl), Pyrimidinyl (e.g., 4-pyrimidinyl), pyrazinyl (e.g., 2-pyrazinyl), Cinnolinyl (e.g., 3-cinnolinyl), phthaladinyl (e.g., 5-phthaladinyl), Quinazolinyl (e.g., 2-quinazolinyl), isoxazolyl (e.g., 3-isoxazolyl, 4-isoxazolyl), Benzisoxazolyl (e.g., 1,2-benzisoxazol-4-yl, 2,1-benzisoxazol-3-yl), oxazolyl (e.g., 2-oxazolyl, 4-oxazolyl, 5-oxazolyl), benzoxazolyl (e.g., 2-benzoxazolyl), Benzoxadiazolyl (e.g., 4-benzoxadiazolyl), isothiazolyl (e.g., 3-isothiazolyl, 4-isothiazolyl) benzisothiazolyl (e.g., 1,2-benzisothiazol-3-yl, 2,1-benzisothiazol-5-yl), thiazolyl (e.g., 2-thiazolyl), benzothiazolyl (e.g., 2-benzothiazolyl), Thiadiazolyl (e.g., 1,2,3-thiadiazol-4-yl), oxadiazolyl (e.g., 1,3,4-oxadiazol-2-yl), Dihydroxadiazolyl (e.g., 4,5-dihydro-1,2,4-oxadiazol-3-yl), furyl (e.g. 2-furyl, 3-furyl), benzofuryl (e.g., 3-benzofuryl), isobenzofuryl (e.g., 1-isobenzofuryl), Thienyl (e.g., 2-thienyl, 3-thienyl), benzothienyl (1-benzothiophene-2-yl, 2-benzothiophen-1-yl), tetrazolyl (e.g., 5-tetrazolyl), benzodioxolyl (e.g., 1,3-benzodioxol-5-yl), Dibenzofuryl (e.g., 2-dibenzofuryl, 3-dibenzofuryl), dibenzoxepinyl (e.g., dibenz [b, f] oxepin-2-yl), dihydrodibenzoxepinyl (e.g., dihydrodibenz [b, f] oxepin-2-yl, Chromenyl (e.g., 2H-chromene-3-yl, 4H-chromene-2-yl), dibenzothiepinyl (e.g., dibenzo [b, f] thiepin-3-yl, dihydrodibenzo [b, f] thiepin-3-yl), morpholinyl (e.g., 1,4-morpholin-4-yl), phenothiadinyl (2-phenothiadinyl), cyclopentathienyl (e.g., cyclopenta [b] thiophen-3-yl), cyclohexathienyl (e.g., cyclohexa [b] thiophen-3-yl), Cycloheptathienyl (e.g., cyclohepta [b] thiophen-3-yl), dibenzothienyl (e.g., 2-dibenzothienyl), dibenzopyranyl (e.g., 2-dibenzopyranyl), Dibenzo-p-dioxyl (e.g., 2-dibenzo-p-dioxyl) and the like.

Der Begriff „Cycloalkyl" bedeutet ein cyclisches C3-C8-Alkyl, zum Beispiel Cyclopropyl, Cyclobutyl, Cyclopentyl, Cyclohexyl und dergleichen.The term "cycloalkyl" means C 3 -C 8 alkyl, a cyclic C, for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and the like.

Der Begriff „Cycloalkenyl" bedeutet ein cyclisches C3-C8-Alkenyl, zum Beispiel Cyclopropenyl (z.B. 1-Cyclopropenyl), Cyclobutenyl (z.B. 2-Cyclobuten-1-yl), Cyclopentenyl (1-Cyclopenten-1-yl), Cyclohexenyl (1-Cyclohexen-1-yl) und dergleichen.The term "cycloalkenyl" means a cyclic C 3 -C 8 alkenyl, for example cyclopropenyl (eg 1-cyclopropenyl), cyclobutenyl (eg 2-cyclobuten-1-yl), cyclopentenyl (1-cyclopenten-1-yl), cyclohexenyl (1-cyclohexen-1-yl) and the like.

Der Begriff „Alkoxy" bedeutet C1-C6-Alkoxy, zum Beispiel Methoxy, Ethoxy, n-Propoxy, i-Propoxy, n-Butoxy und dergleichen.The term "alkoxy" means C 1 -C 6 alkoxy, for example methoxy, ethoxy, n-propoxy, i -propoxy, n-butoxy and the like.

Beispiele für das substituierte Amino in der Definition von „substituiertem oder unsubstituiertem Amino" schließen mono- oder disubstituiertes Amino wie Methylamino, Ethylamino, Dimethylamino, Cyclohexylamino, Phenylamino, Diphenylamino oder cyclisches Amino wie Piperidino, Piperadino oder Morpholino ein.Examples for the substituted amino in the definition of "substituted or unsubstituted Amino "close mono- or disubstituted amino such as methylamino, ethylamino, dimethylamino, Cyclohexylamino, phenylamino, diphenylamino or cyclic amino such as piperidino, piperadino or morpholino.

Der Begriff „Acyloxy" bedeutet ein Acyloxy, das sich von dem vorstehenden „Acyl" ableitet, zum Beispiel Acetyloxy, Propionyloxy, Butyryloxy, Valeryloxy und dergleichen.Of the Term "acyloxy" means an acyloxy, which is derived from the above "acyl", for example Acetyloxy, propionyloxy, butyryloxy, valeryloxy and the like.

Der Begriff „Halogen" bedeutet Fluor, Chlor, Brom und Iod.Of the Term "halogen" means fluorine, Chlorine, bromine and iodine.

Der Begriff „Alkoxycarbonyl" bedeutet einen Alkoxycarbonylrest, der sich von dem vorstehenden „Alkoxy" ableitet, zum Beispiel Methoxycarbonyl, Ethoxycarbonyl, Phenyloxycarbonyl und dergleichen.Of the Term "alkoxycarbonyl" means an alkoxycarbonyl radical, which is derived from the above "alkoxy", for example Methoxycarbonyl, ethoxycarbonyl, phenyloxycarbonyl and the like.

Der Begriff „Aralkyloxycarbonyl" bedeutet einen Aralkyloxycarbonylrest, der sich von dem vorstehenden „Aralkyl" ableitet, zum Beispiel Benzyloxycarbonyl, Phenethyloxycarbonyl und dergleichen.Of the Term "aralkyloxycarbonyl" means an aralkyloxycarbonyl radical, which is derived from the above "aralkyl", for example Benzyloxycarbonyl, phenethyloxycarbonyl and the like.

Der Begriff „Aryloxycarbonyl" bedeutet einen Aryloxycarbonylrest, der sich von dem vorstehenden „Aryl" ableitet, zum Beispiel Phenyloxycarbonyl, Naphthyloxycarbonyl und dergleichen.Of the Term "aryloxycarbonyl" means an aryloxycarbonyl radical, which is derived from the above "aryl", for example Phenyloxycarbonyl, naphthyloxycarbonyl and the like.

Der Begriff „Alkenyloxy" bedeutet einen Alkenyloxyrest, der sich von dem vorstehenden „Alkenyl" ableitet, zum Beispiel Vinyloxy, 1-Propenyloxy, 2-Butenyloxy und dergleichen.Of the Term "alkenyloxy" means an alkenyloxy radical, which is derived from the above "alkenyl", for example Vinyloxy, 1-propenyloxy, 2-butenyloxy and the like.

Der Begriff „Hydroxyalkyl" bedeutet einen Hydroxyalkylrest, der sich von dem vorstehenden „Alkyl" ableitet, zum Beispiel Hydroxymethyl, Hydroxyethyl, Hydroxypropyl und dergleichen.Of the Term "hydroxyalkyl" means a hydroxyalkyl radical, which is derived from the above "alkyl", for example Hydroxymethyl, hydroxyethyl, hydroxypropyl and the like.

Der Begriff „Alkylthio" bedeutet einen Alkylthiorest, der sich von dem vorstehenden „Alkyl" ableitet, zum Beispiel Methylthio, Ethylthio, Propylthio und dergleichen.Of the Term "alkylthio" means an alkylthio radical, which is derived from the above "alkyl", for example Methylthio, ethylthio, propylthio and the like.

Der Begriff „Alkylendioxy" bedeutet C1-C3-Alkylendioxy, zum Beispiel Methylendioxy, Ethylendioxy, Propylendioxy und dergleichen.The term "alkylenedioxy" means C 1 -C 3 -alkylenedioxy, for example methylenedioxy, ethylenedioxy, propylenedioxy and the like.

Im Falle von „Phenylen", „Naphthylen", „Thiophendiyl", „Indoldiyl", „Oxazoldiyl", „Oxadiazoldiyl" und „Tetrazoldiyl" kann der Rest zu den benachbarten Resten an jeder der zwei substituierbaren Stellen binden.in the Traps of "phenylene", "naphthylene", "thiophenediyl", "indolediyl", "oxazolediyl", "oxadiazolediyl" and "tetrazolediyl" may be the radical to the adjacent residues at each of the two substitutable sites tie.

Wenn ein Substituent(en) cyclisch ist, kann er in den vorstehenden Definitionen mit einem bis drei Substituenten substituiert werden, ausgewählt aus Nitro, Alkoxy, Sulfamoyl, substituiertem oder unsubstituiertem Amino, Acyl, Acyloxy, Hydroxy, Halogen, Alkyl, Alkinyl, Carboxy, Alkoxycarbonyl, Aralkoxycarbonyl, Aryloxycarbonyl, Mesyloxy, Cyano, Alkenyloxy, Hydroxyalkyl, Trifluormethyl, Alkylthio, -N=PPh3, Oxo, Thioxo, Hydroxyimino, Alkoxyimino, Phenyl und Alkylendioxy. Der/die Substituent(en) kann an jeder geeigneten Position an den Ring binden.When a substituent (s) is cyclic, it may be substituted in the above definitions with one to three substituents selected from nitro, alkoxy, sulfamoyl, substituted or unsubstituted amino, acyl, acyloxy, hydroxy, halogen, alkyl, alkynyl, carboxy, Alkoxycarbonyl, aralkoxycarbonyl, aryloxycarbonyl, mesyloxy, cyano, alkenyloxy, hydroxyalkyl, trifluoromethyl, alkylthio, -N = PPh 3 , oxo, thioxo, hydroxyimino, alkoxyimino, phenyl and alkylenedioxy. The substituent (s) may bind to the ring at any suitable position.

Beispiele für Salze der Verbindung (Ib) schließen jene ein, die mit einem Alkalimetall (z.B. Lithium, Natrium oder Kalium), einem Erdalkalimetall (z.B. Calcium), einer organischen Base (z.B. Tromethamin, Trimethylamin, Triethylamin, 2-Aminobutan, t-Butylamin, Diisopropylethylamin, n-Butylmethylamin, Cyclohexylamin, Dicyclohexylamin, N-Isopropylcyclohexylamin, Furfurylamin, Benzylamin, Methylbenzylamin, Dibenzylamin, N,N-Dimethylbenzylamin, 2-Chlorbenzylamin, 4-Methoxybenzylamin, 1-Naphthylenmethylamin, Diphenylbenzylamin, Triphenylamin, 1-Naphthylamin, 1-Aminoanthoracen, 2-Aminoanthoracen, Dehydroabiethylamin, N-Methylmorpholin oder Pyridin), einer Aminosäure (z.B. Lysin oder Arginin) und dergleichen gebildet werden.Examples for salts close the compound (Ib) those which are reacted with an alkali metal (e.g., lithium, sodium or Potassium), an alkaline earth metal (e.g., calcium), an organic Base (e.g., tromethamine, trimethylamine, triethylamine, 2-aminobutane, t-butylamine, diisopropylethylamine, n-butylmethylamine, cyclohexylamine, dicyclohexylamine, N-isopropylcyclohexylamine, furfurylamine, benzylamine, methylbenzylamine, Dibenzylamine, N, N-dimethylbenzylamine, 2-chlorobenzylamine, 4-methoxybenzylamine, 1-Naphthylenemethylamine, diphenylbenzylamine, triphenylamine, 1-naphthylamine, 1-aminoanthoracene, 2-aminoanthoracene, dehydroabiethylamine, N-methylmorpholine or pyridine), one amino acid (e.g., lysine or arginine) and the like.

Der Begriff „Hydrat" bedeutet ein Hydrat der Verbindung der Formel (Ib) oder ihres Salzes. Beispiele schließen Mono- und Dihydrate ein.Of the Term "hydrate" means a hydrate the compound of formula (Ib) or its salt. Examples include mono and dihydrates.

Die vorliegenden Verbindungen werden durch die Formel (Ib) gezeigt und schließen die Form jeglicher Arten von Stereoisomeren (z.B. Diastereomer, Epimer, Enantiomer) und racemischer Verbindungen ein.The Present compounds are shown by the formula (Ib) and shut down the form of any kind of stereoisomers (e.g., diastereomer, Epimer, enantiomer) and racemic compounds.

Verbindungen der allgemeinen Formel (Ib) können wie nachstehend gezeigt durch Umsetzen einer Aminoverbindung der allgemeinen Formel (II) mit einem reaktiven Derivat der Sulfonsäure oder Carbonsäuren entsprechend der Teilstruktur: Z-X1-X2-X3 hergestellt werden.Compounds of the general formula (Ib) can be prepared as shown below by reacting an amino compound of the general formula (II) with a reactive derivative of the sulfonic acid or carboxylic acids corresponding to the partial structure: ZX 1 -X 2 -X 3 .

Figure 00110001
Figure 00110001

Wobei A, B, R, X1, X2, X3, Y wie vorstehend definiert sind, und Z für -CO- steht.Wherein A, B, R, X 1 , X 2 , X 3 , Y are as defined above, and Z is -CO-.

Eine Carbonsäure, die der Teilstruktur entspricht, ist eine Verbindung der allgemeinen Formel X3-X2-X1-COOH. Ein reaktives Derivat dieser Carbonsäuren bedeutet ein entsprechendes Halogenid (z.B. Chlorid, Bromid, Iodid), Säureanhydrid (z.B. gemischtes Säureanhydrid mit Ameisensäure oder Essigsäure), ein Aktivester (z.B. Succinimidester), und Beispiele davon schließen im Allgemeinen Acylierungsmittel ein, die zur Acylierung von Aminogruppen verwendet werden. Die Carbonsäuren X3-X2-X1-COOH können bei der Umsetzung als solche ohne Umwandlung in ein reaktives Derivat verwendet werden, in der Gegenwart eines Kondensationsmittels (z.B. Dicyclohexylcarbodiimid (DCC), 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimid, N,N'-Carbonyldiimidazol), welches bei der Kondensationsreaktion zwischen einem Amin und einer Carbonsäure verwendet wird.A carboxylic acid corresponding to the partial structure is a compound of the general formula X 3 -X 2 -X 1 -COOH. A reactive derivative of these carboxylic acids means a corresponding halide (eg, chloride, bromide, iodide), acid anhydride (eg, mixed acid anhydride with formic acid or acetic acid), an active ester (eg, succinimide ester), and examples thereof generally include acylating agents that are used to acylate amino groups be used. The carboxylic acids X 3 -X 2 -X 1 -COOH can be used in the reaction as such without conversion to a reactive derivative, in the presence of a condensing agent (eg dicyclohexylcarbodiimide (DCC), 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide, N, N'-carbonyldiimidazole) used in the condensation reaction between an amine and a carboxylic acid.

Die Umsetzung kann unter Bedingungen durchgeführt werden, die allgemein bei der Acylierung von Aminogruppen verwendet werden. Zum Beispiel wird im Falle der Kondensation unter Verwendung eines Säurehalogenids die Umsetzung unter Verwendung eines Lösungsmittels wie einem Etherlösungsmittel (z.B. Diethylether, Tetrahydrofuran, Dioxan), Benzollösungsmittel (z.B. Benzol, Toluol, Xylol), halogenierten Kohlenwasserstofflösungsmittel (z.B. Dichlormethan, Dichlorethan, Chloroform), Ethylacetat, Dimethylformamid, Dimethylsulfoxid, Acetonitril oder dergleichen, gegebenenfalls in der Gegenwart einer Base (z.B. organischer Base wie Triethylamin, Pyridin, N,N-Dimethylaminopyridin, N-Methylmorpholin; anorganischer Base wie Natriumhydroxid, Kaliumhydroxid, Kaliumcarbonat oder dergleichen) unter Kühlung, bei Raumtemperatur oder unter Erhitzen, bevorzugt bei einer Temperatur im Bereich von –20°C bis zu einer Temperatur unter Kühlung oder von Raumtemperatur bis zur Rückflusstemperatur des Reaktionssystems, für mehrere Min. bis zu mehreren Std., vorzugsweise für 0,5 Std. bis zu 24 Std., stärker bevorzugt für 1 Std. bis zu 12 Std. durchgeführt.The Implementation can be carried out under conditions commonly encountered the acylation of amino groups can be used. For example, will in the case of condensation using an acid halide the reaction using a solvent such as an ether solvent (e.g., diethyl ether, tetrahydrofuran, dioxane), benzene solvent (e.g., benzene, toluene, xylene), halogenated hydrocarbon solvents (e.g., dichloromethane, dichloroethane, chloroform), ethyl acetate, dimethylformamide, Dimethyl sulfoxide, acetonitrile or the like, optionally in the presence of a base (e.g., organic base such as triethylamine, Pyridine, N, N-dimethylaminopyridine, N-methylmorpholine; inorganic base such as sodium hydroxide, potassium hydroxide, Potassium carbonate or the like) under cooling, at room temperature or under heating, preferably at a temperature in the range of -20 ° C up to a temperature under cooling or from room temperature to the reflux temperature of the reaction system, for many Min. Up to several hours, preferably for 0.5 hours up to 24 hours, stronger preferred for 1 hour up to 12 hours.

Die Reaktionsbedingungen für die Umsetzung zwischen einem anderen reaktiven Derivat oder einer freien Säure und einem Amin (II) können auf eine herkömmliche Weise abhängig von den Charakteristika des jeweiligen reaktiven Derivats oder freien Säure festgelegt werden.The Reaction conditions for the reaction between another reactive derivative or a free one Acid and an amine (II) can on a conventional Way dependent from the characteristics of the particular reactive derivative or free Acid set become.

Das Reaktionsprodukt kann durch herkömmliche Reinigungsverfahren, zum Beispiel der Extraktion mit einem Lösungsmittel, Chromatographie, Umkristallisation oder dergleichen gereinigt werden.The Reaction product can by conventional Cleaning process, for example extraction with a solvent, Chromatography, recrystallization or the like.

Spezifische Beispiele der Verbindung (II) als Startmaterial für das vorliegende Verfahren sind wie nachstehend. Beispiele für eine 3-Amino[2.2.1]bicyclische Verbindung schließen 7-(3-Aminobicyclo[2.2.1]hept-2-yl)-5-heptensäure, 7-(3-Aminobicyclo[2.2.1]hept-2-yl)-2,2-dimethyl-5-heptensäure, 7-(N-Methyl-3-aminobicyclo[2.2.1]hept-2-yl)-5-heptensäure, 6-(3- Aminobicyclo[2.2.1]hept-2-yl)-5-hexensäure ein. Spezifische Beispiele für eine 2-Amino-6,6-dimethyl[3.1.1]bicyclische Verbindung schließen 7-(2-Amino-6,6-dimethylbicyclo[3.1.1]hept-3-yl)-5-heptensäure ein. In diesen Startverbindungen kann die Heptensäurekette gesättigt sein, um eine Heptansäurekette zu bilden, unterbrochen durch ein Heteroatom(e) oder eine Heterogruppe(n) wie -O-, -S-, -NH- oder einem Phenylen(e) oder substituiert mit einer Oxogruppe. Beispiele derartiger Verbindungen schließen 7-(3-Aminobicyclo[2.2.1]hept-2-yl)heptansäure, 4-[2-(2-Aminobicyclo[3.1.1]hept-3-yl)ethoxyphenylessigsäure, 7-(3-Aminobicyclo[2.2.1]hept-2-yl)-6-oxoheptansäure ein. Diese Startverbindungen werden entweder in der japanischen Offenlegungsschrift Nr. JP 63-139161 oder JP 01-52751 beschrieben oder können gemäß dem darin beschriebenen Verfahren hergestellt werden.specific Examples of the compound (II) as a starting material for the present invention Procedures are as below. Examples of a 3-amino [2.2.1] bicyclic Close connection 7- (3-Aminobicyclo [2.2.1] hept-2-yl) -5-heptenoic acid, 7- (3-aminobicyclo [2.2.1] hept-2-yl) -2,2-dimethyl-5-heptenoic acid, 7- (N-methyl-3-aminobicyclo [2.2.1] hept-2-yl) -5-heptenoic acid, 6- (3-aminobicyclo [2.2.1] hept-2-yl) -5-hexenoic acid. specific examples for a 2-amino-6,6-dimethyl [3.1.1] bicyclic Close connection 7- (2-amino-6,6-dimethylbicyclo [3.1.1] hept-3-yl) -5-heptenoic acid. In these starting connections can the heptenoic acid chain saturated be a heptanoic acid chain interrupted by a heteroatom (s) or a hetero group (s) such as -O-, -S-, -NH- or a phenylene (s) or substituted with an oxo group. Examples of such compounds include 7- (3-aminobicyclo [2.2.1] hept-2-yl) heptanoic acid, 4- [2- (2-aminobicyclo [3.1.1] hept-3-yl) ethoxyphenylacetic acid, 7- (3 Aminobicyclo [2.2.1] hept-2-yl) -6-oxoheptanoic acid. These starting compounds are disclosed either in Japanese Laid-Open Publication Nos. JP 63-139161 or JP 01-52751 or can according to the therein be prepared described methods.

Eine Carbonsäure X3-X2-X1-COOH, die der Partialstruktur Z-X1-X2-X3 entspricht, bedeutet eine Carbonsäure mit Substituenten, die den vorstehenden Reste X entsprechen. Das heißt, dass die Beispiele Alkancarbonsäuren, Alkencarbonsäuren, Alkincarbonsäuren, Cycloalkancarbonsäuren, Cycloalkencarbonsäuren, Arylcarbonsäuren, Aralkyloxycarbonsäuren, heterocyclisch substituierte Carbonsäuren, Heteroarylalkylcarbonsäuren und substituierte Aminocarbonsäuren einschließen. Jede der Carbonsäuren kann einen (mehrere) der vorstehenden Substituenten aufweisen. Diese Carbonsäuren sind im Handel erhältlich oder können einfach aus einer bekannten Verbindungen) gemäß einem bekannten Verfahren synthetisiert werden. Nach der Umsetzung kann die Carbonsäure gegebenenfalls in das entsprechende vorstehende reaktive Derivat umgewandelt werden. Wenn zum Beispiel ein Säurehalogenid benötigt wird, wird die Verbindung mit einem Thionylhalogenid (z.B. Thionylchlorid), Phosphorhalogenid (z.B. Phosphortrichlorid, Phosphorpentachlorid) oder Oxalylhalogenid (z.B. Oxalylchlorid) gemäß einem bekannten Verfahren wie jenem, das in der Literatur (z.B. Shin-Jikken-Kagaku-Koza, Vol. 14, S. 1787 (1978), Synthesis, 852–854 (1986); Shin-Jikken-Kagaku-Koza, Vol. 22, S. 115 (1992)) beschrieben wird, umgesetzt. Auch die anderen reaktiven Derivate können gemäß den bekannten Verfahren hergestellt werden.A carboxylic acid X 3 -X 2 -X 1 -COOH corresponding to the partial structure ZX 1 -X 2 -X 3 means a carboxylic acid having substituents corresponding to the above X radicals. That is, the examples include alkanecarboxylic acids, alkenecarboxylic acids, alkynecarboxylic acids, cycloalkane carboxylic acids, cycloalkenecarboxylic acids, arylcarboxylic acids, aralkyloxycarboxylic acids, heterocyclic substituted carboxylic acids, heteroarylalkylcarboxylic acids, and substituted aminocarboxylic acids. Each of the carboxylic acids may have one (more) of the above substituents. These carboxylic acids are commercially available or can be easily synthesized from a known compound according to a known method. After the reaction, the carboxylic acid may optionally be converted to the corresponding reactive derivative above. For example, when an acid halide is needed, the compound is reacted with a thionyl halide (eg, thionyl chloride), phosphorus halide (eg, phosphorus trichloride, phosphorus pentachloride) or oxalyl halide (eg, oxalyl chloride) according to a known method such as that described in the literature (eg, Shin-Jikken-Kagaku Koza, Vol. 14, p. 1787 (1978), Synthesis, 852-854 (1986); Shin-Jikken-Kagaku-Koza, Vol. 22, p. 115 (1992)). The other reactive derivatives can also be prepared according to the known methods.

Unter den Zielverbindungen (Ib) können jene, in welchen die Seitenkette A eine ungesättigte Bindung, hauptsächlich eine Doppelbindung enthält, auch durch Umsetzen eines Aldehydderivats der nachstehenden allgemeinen Formel (III) mit einer Ylid-Verbindung, die dem Rest der Seitenkette A-R entspricht, unter Wittig-Reaktionsbedingungen:

Figure 00140001
wobei A, B, R, X1, X2, X3, Y wie vorstehend definiert sind, und Z für -CO- steht, hergestellt werden.Among the object compounds (Ib), those in which the side chain A contains an unsaturated bond, mainly a double bond, can also be obtained by reacting an aldehyde derivative of the following general formula (III) with an ylide compound corresponding to the rest of the side chain AR Wittig reaction conditions:
Figure 00140001
wherein A, B, R, X 1 , X 2 , X 3 , Y are as defined above, and Z is -CO-.

Die Startverbindung (III) kann gemäß einem zum Beispiel in der japanischen Offenlegungsschrift Nr. JP 02-256650 beschriebenen Verfahren hergestellt werden. Weiterhin kann eine Ylid-Verbindung, die dem Rest der Seitenkette A-R entspricht, durch Umsetzen eines Triphenylphosphins mit einer entsprechenden halogenierten Alkansäure oder einem Esterderivat, Etherderivat oder Amidderivat davon in der Gegenwart einer Base gemäß einem bekannten Verfahren synthetisiert werden.The Starting compound (III) may be prepared according to a For example, in Japanese Patent Laid-Open Publication No. JP 02-256650 be prepared described methods. Furthermore, a Ylide compound, which corresponds to the rest of the side chain A-R, by reacting a Triphenylphosphine with a corresponding halogenated alkanoic acid or an ester derivative, ether derivative or amide derivative thereof in the presence a base according to one be synthesized known methods.

Unter den Zielverbindungen (Ib) können jene, wobei R COOH ist, falls gewünscht in ein entsprechendes Esterderivat, Alkoholderivat, Etherderivat, Amidderivat umgewandelt werden. Zum Beispiel können Esterderivate durch Veresterung von Carbonsäuren auf eine herkömmlich Weise hergestellt werden. Ein Esterderivat, wenn es reduziert wird, ergibt ein Alkoholderivat und wenn es amidiert wird, ergibt es ein Amidderivat. Ein Etherderivat kann durch O-Alkylierung eines Alkoholderivats erhalten werden.Under the target compounds (Ib) can those where R is COOH, if desired in a corresponding one Ester derivative, alcohol derivative, ether derivative, amide derivative converted become. For example, you can Ester derivatives by esterification of carboxylic acids in a conventional manner getting produced. An ester derivative, when reduced, gives an alcohol derivative and when amidated gives an amide derivative. An ether derivative can be prepared by O-alkylation of an alcohol derivative to be obtained.

Die Verbindung (Ib) der vorliegenden Erfindung weist in vitro eine antagonistische Wirkung gegen PGD2 durch die Bindung an den PGD2-Rezeptor auf und ist als ein Arzneistoff zur Behandlung von Krankheiten nützlich, in welchen eine Fehlfunktion der Mastzellen aufgrund einer übermäßigen Produktion von PGD2 beteiligt ist. Zum Beispiel ist die Verbindung (Ib) als ein Arzneistoff zur Behandlung von Krankheiten wie systemischer Mastozytose und Störung der systemischen Mastzellaktivierung und auch trachealer Kontraktion, Asthma, allergischer Rhinitis, allergischer Konjunktivitis, Urtikaria, Verletzungen aufgrund von Ischämie-Reperfusion und Entzündung nützlich. Die Verbindung (Ib) weist in vivo eine präventive Wirkung bei Nasenokklusion auf und ist deshalb als ein Arzneistoff zu deren Behandlung besonders nützlich.The compound (Ib) of the present invention has an antagonistic activity against PGD 2 in vitro by binding to the PGD 2 receptor and is useful as a drug for the treatment of diseases in which mast cell dysfunction due to excessive production of PGD 2 is involved. For example, the compound (Ib) is useful as a drug for the treatment of diseases such as systemic mastocytosis and disorder of systemic mast cell activation and also tracheal contraction, asthma, allergic rhinitis, allergic conjunctivitis, urticaria, ischemia-reperfusion injury and inflammation. The compound (Ib) has a preventive effect in nasal occlusion in vivo and is therefore particularly useful as a drug for the treatment thereof.

Wird eine Verbindung (Ib) der vorliegenden Erfindung bei der Behandlung verwendet, kann sie in üblichen Formulierungen für die orale und parenterale Verabreichung formuliert werden. Ein Arzneimittel, das eine Verbindung (Ib) der vorliegenden Erfindung enthält, kann in der Form einer oralen und parenteralen Verabreichung vorliegen. Konkret kann sie in Formulierungen für die orale Verabreichung wie Tabletten, Kapseln, Granulate, Pulver, Sirup und dergleichen; jenen für die parenterale Verabreichung wie injizierbare Lösungen oder Suspensionen zur intravenösen, intramuskulären oder subkutanen Injektion, Inhalationsmittel, Augentropfen, Nasentropfen, Suppositorien oder perkutane Formulierungen wie Salben formuliert werden.Becomes a compound (Ib) of the present invention in the treatment used, it can in usual Formulations for oral and parenteral administration can be formulated. A medicine, which contains a compound (Ib) of the present invention in the form of oral and parenteral administration. Specifically, it can be used in formulations for oral administration Tablets, capsules, granules, powders, syrups and the like; those for the parenteral administration such as injectable solutions or suspensions intravenous, intramuscular or subcutaneous injection, inhalants, eye drops, nasal drops, Suppositories or percutaneous formulations such as salves are formulated become.

Bei der Herstellung der Formulierungen können Träger, Exzipienten, Lösungsmittel und Grundlagen, die einem Fachmann bekannt sind, verwendet werden. Handelt es sich um Tabletten, werden diese durch Verpressen oder Formulieren eines wirksamen Bestandteils zusammen mit Hilfskomponenten hergestellt. Beispiele für verwendbare Hilfskomponenten schließen pharmazeutisch verträgliche Exzipienten wie Bindemittel (z.B. Maisstärke), Füllstoffe (z.B. Lactose, mikrokristalline Cellulose), Sprengmittel (z.B. Natriumstärkeglycolat) oder Gleitmittel (z.B. Magnesiumstearat) ein. Tabletten können passend überzogen werden. Handelt es sich um flüssige Formulierungen wie Sirupe, Lösungen oder Suspensionen können diese Suspensionsmittel (z.B. Methylcellulose), Emulgatoren (z.B. Lecithin), Konservierungsmittel und dergleichen enthalten. Handelt es sich um injizierbare Formulierungen, können diese in Form einer Lösung oder Suspension oder einer öligen oder wässrigen Emulsion sein, welche ein Mittel zur Stabilisierung der Suspension oder Dispergiermittel und dergleichen enthalten können. Handelt es sich um ein Inhalationsmittel, wird es in einer flüssigen Formulierung formuliert, die in einem Inhalator anwendbar ist. Handelt es sich um Augentropfen, werden diese in einer Lösung oder einer Suspension formuliert. Handelt es sich insbesondere um einen nasalen Arzneistoff zur Behandlung von Nasenokklusion, kann dieser als eine Lösung oder Suspension, die durch herkömmliche Formulierungsverfahren hergestellt wird, oder als ein unter Verwendung eines pulverisierenden Mittels (z.B. Hydroxypropylcellulose, Carbopol) formuliertes Pulver verwendet werden, welche in die Nasenhöhle verabreicht werden. In einer anderen Ausführungsform kann er als ein Aerosol nach Abfüllen in einen Spezialbehälter zusammen mit einem Lösungsmittel mit niederem Siedepunkt verwendet werden.at The preparation of the formulations may include carriers, excipients, solvents and basics known to those skilled in the art. In the case of tablets, these are obtained by compression or Formulate an active ingredient together with auxiliary components produced. examples for Useful auxiliary components include pharmaceutically acceptable excipients such as binders (e.g., cornstarch), fillers (e.g., lactose, microcrystalline cellulose), disintegrants (e.g., sodium starch glycolate) or Lubricant (e.g., magnesium stearate). Tablets can be coated appropriately become. Is it liquid Formulations like syrups, solutions or suspensions can these suspending agents (e.g., methyl cellulose), emulsifiers (e.g. Lecithin), preservatives and the like. These These are injectable formulations, these may be in the form of a solution or Suspension or oily or aqueous Emulsion, which is a means of stabilizing the suspension or dispersants and the like. These it is an inhalant, it is formulated in a liquid formulation, which is applicable in an inhaler. Are they eye drops, These are in a solution or formulated in a suspension. Is it in particular about a nasal drug for the treatment of nasal occlusion this as a solution or suspension by conventional Formulation process is prepared, or as a using a pulverizing agent (e.g., hydroxypropyl cellulose, Carbopol) formulated powders which are administered into the nasal cavity. In another embodiment he can after filling as an aerosol in a special container together with a solvent be used with low boiling point.

Obwohl eine passende Dosierung der Verbindung (Ib), abhängig vom Weg der Verabreichung, Alter, Körpergewicht, Geschlecht oder Zustand des Patienten und der Art des/der Arzneistoff/Arzneistoffe, die, wenn überhaupt, zusammen verwendet werden variiert und am Ende durch den Arzt bestimmt werden sollte, kann die tägliche Dosierung im Falle der oralen Verabreichung, im Allgemeinen zwischen etwa 0,01–100 mg, bevorzugt etwa 0,01–10 mg, stärker bevorzugt etwa 0,1–10 mg pro kg Körpergewicht liegen. Im Falle der parenteralen Verabreichung kann die tägliche Dosierung im Allgemeinen zwischen etwa 0,001–100 mg, bevorzugt etwa 0,001–1 mg, stärker bevorzugt etwa 0,01–1 mg pro kg Körpergewicht liegen. Die tägliche Dosierung kann in 1–4 Aufteilungen verabreicht werden.Even though a suitable dosage of the compound (Ib), depending on the route of administration, Age, body weight, Gender or condition of the patient and the nature of the drug (s), which, if any, used together varies and in the end determined by the doctor should be, can the daily Dosage in case of oral administration, generally between about 0.01-100 mg, preferably about 0.01-10 mg, stronger preferably about 0.1-10 mg per kg of body weight lie. In case of parenteral administration, the daily dosage generally between about 0.001-100 mg, preferably about 0.001-1 mg, more preferably about 0.01-1 mg per kg of body weight lie. The daily Dosage can be in 1-4 Distributions are administered.

Die nachstehenden Beispiele werden bereitgestellt, um die vorliegende Erfindung weiter zu veranschaulichen und sollten nicht als Beschränkung des Bereichs davon ausgelegt werden.The following examples are provided to further further the present invention and should not be construed as limiting the scope thereof.

Beispiel 1

Figure 00160001
example 1
Figure 00160001

Methyl-(Z)-7-[(1S,2R,3R,4R)-3-aminobicyclo[2.2.1]hept-2-yl]-5-heptenoattrifluoracetat (II-2) (232 mg, 0,636 mmol), welches durch das in Referenzbeispiel 4 der japanischen Offenlegungsschrift Nr. JP 63-139161 beschriebene Verfahren hergestellt wurde, wurde in Methylenchlorid (5 ml) gelöst. Zu der Lösung wurde unter Eiskühlung Triethylamin (0,279 ml, 2,00 mmol) und 4-Biphenylcarbonylchlorid gegeben und für 7 Std. bei der gleichen Temperatur gerührt. Das Reaktionsgemisch wurde durch Säulenchromatographie über Kieselgel (Ethylacetat/n-Hexan (1:4)) gereinigt, um Methyl-(Z)-7-[(1S,2R,3R,4R)-3-(4-biphenyl)carbonylaminobicyclo[2.2.1]hept-2-yl]-5-heptenoat (1k-11) (221 mg, 0,512 mmol) zu ergeben. Die Verbindung (1k-11) (190 mg, 0,440 mmol) wurde in Methanol (6 ml) gelöst. Zu der Lösung wurde unter Eiskühlung 1 N KOH (1,10 ml, 1,10 mmol) gegeben und für 15 Std. bei Raumtemperatur gerührt. Das Reaktionsgemisch wurde im Vakuum aufkonzentriert. Der Rückstand wurde, nach Zugabe von Wasser (20 ml) und 1 N HCl (2 ml), mit Ethylacetat extrahiert. Die organische Phase wurde mit gesättigter Kochsalzlösung gewaschen, über wasserfreiem Natriumsulfat getrocknet und aufkonzentriert. Der Rückstand wurde durch Säulenchromatographie über Kieselgel (Ethylacetat/Hexan (1:1), enthält 0,3% Essigsäure) gereinigt, um (Z)-7-[(1S,2R,3R,4R)-3-(4-Biphenyl)carbonylaminobicyclo[2.2.1]hept-2-yl]-5-heptensäure (1k-12) (172 mg, 0,412 mmol) zu ergeben, Ausbeute 94%.Methyl (Z) -7 - [(1S, 2R, 3R, 4R) -3-aminobicyclo [2.2.1] hept-2-yl] -5-heptenoattrifluoracetat (II-2) (232 mg, 0.636 mmol), which is characterized by that shown in Reference Example 4 of Japanese Patent Laid-Open Publication No. 63-139161 Was prepared, was dissolved in methylene chloride (5 ml). To the solution was under ice-cooling Triethylamine (0.279 mL, 2.00 mmol) and 4-biphenylcarbonyl chloride, and for 7 hours stirred at the same temperature. The reaction mixture was purified by column chromatography on silica gel (ethyl acetate / n-hexane (1: 4)) to give methyl (Z) -7 - [(1S, 2R, 3R, 4R) -3- (4-biphenyl) carbonylaminobicyclo [2.2.1] hept-2-yl] -5- heptenoate (1k-11) (221 mg, 0.512 mmol). The compound (1k-11) (190 mg, 0.440 mmol) was dissolved in methanol (6 ml). Became the solution under ice-cooling Add 1N KOH (1.10 mL, 1.10 mmol) and at room temperature for 15 h touched. The reaction mixture was concentrated in vacuo. The residue After addition of water (20 ml) and 1N HCl (2 ml), ethyl acetate was added extracted. The organic phase was washed with brine, over anhydrous Dried and concentrated sodium sulfate. The residue was purified by column chromatography on silica gel (ethyl acetate / hexane (1: 1) 0.3% acetic acid) purified to give (Z) -7 - [(1S, 2R, 3R, 4R) -3- (4-biphenyl) carbonylaminobicyclo [2.2.1] hept-2-yl] -5-heptenoic acid (1k-12) (172 mg, 0.412 mmol), yield 94%.

Die nachstehenden Verbindungen können auch auf die nachstehende Art und Weise hergestellt werden.The the following compounds also be made in the following manner.

Die gemäß einem in dem vorstehenden Beispiel beschriebenen Verfahren hergestellten Verbindungen werden in den nachstehenden Tabellen gezeigt.The according to one prepared in the above example Compounds are shown in the tables below.

Tabelle 1k

Figure 00180001
Table 1k
Figure 00180001

Figure 00190001
Figure 00190001

Tabelle 1m

Figure 00200001
Table 1m
Figure 00200001

Figure 00210001
Figure 00210001

Figure 00220001
Figure 00220001

Tabelle 2a

Figure 00230001
Table 2a
Figure 00230001

Figure 00240001
Figure 00240001

Figure 00250001
Figure 00250001

Figure 00260001
Figure 00260001

Figure 00270001
Figure 00270001

Figure 00280001
Figure 00280001

Figure 00290001
Figure 00290001

Figure 00300001
Figure 00300001

Figure 00310001
Figure 00310001

Figure 00320001
Figure 00320001

Figure 00330001
Figure 00330001

Figure 00340001
Figure 00340001

Figure 00350001
Figure 00350001

Figure 00360001
Figure 00360001

Figure 00370001
Figure 00370001

Figure 00380001
Figure 00380001

Figure 00390001
Figure 00390001

Figure 00400001
Figure 00400001

Figure 00410001
Figure 00410001

Figure 00420001
Figure 00420001

Figure 00430001
Figure 00430001

Figure 00440001
Figure 00440001

Figure 00450001
Figure 00450001

Figure 00460001
Figure 00460001

Figure 00470001
Figure 00470001

Tabelle 2b

Figure 00480001
Table 2b
Figure 00480001

Tabelle 2c

Figure 00480002
Table 2c
Figure 00480002

Tabelle 2d

Figure 00480003
Table 2d
Figure 00480003

Tabelle 2e

Figure 00490001
Table 2e
Figure 00490001

Tabelle 2f

Figure 00490002
Table 2f
Figure 00490002

Tabelle 2g

Figure 00490003
Table 2g
Figure 00490003

Tabelle 2h

Figure 00500001
Table 2h
Figure 00500001

Tabelle 2i

Figure 00500002
Table 2i
Figure 00500002

Tabelle 2j

Figure 00510001
Table 2j
Figure 00510001

Tabelle 2k

Figure 00510002
Table 2k
Figure 00510002

Physikalisch-chemische Eigenschaften der vorstehenden Verbindungen werden nachstehend gezeigt. Die nachstehende Verbindungsnummer entspricht der, die in den vorstehenden Tabellen beschrieben wird.
Nr. 1k-1
[α]D = –25,4° (CHCl3, c = 1,08, 23°C).
Nr. 1k-2
CDCl3 200 MHz
1,07–2,28 (14H, m), 2,32 (2H, t, J = 7,4 Hz), 2,63 (1H, m), 3,63 (3H, s), 3,93 (1H, m), 5,30–5,52 (2H, m), 6,35 (1H, d, J = 7,0 Hz), 7,48–7,60 (3H, m), 7,88–8,02 (6H, m).
IR (CHCl3): 3438, 3002, 2946, 2868, 1727, 1652, 1514, 1485, 1363, 1310, 1245, 1154/cm.
[α]D = –80,4° (CHCl3, c = 1,01, 24,0°C).
Nr. 1k-3
CDCl3 200 MHz
1,10–2,26 (14H, m), 2,37 (2H, t, J = 7,2 Hz), 2,60 (1H, m), 3,93 (1H, m), 5,30–5,50 (2H, m), 6,33 (1H, d, J = 7,5 Hz), 7,48–7,58 (3H, m) 7,88 Nr. (6H, m).
IR (CHCl3): 3446, 3004, 2952, 2874, 1709, 1652, 1515, 1485, 1305, 1153/cm.
[α]D = –96,4° (CHCl3, c = 1,05, 23,0°C).
Nr. 1k-4
CDCl3 300 MHz
1,05–2,17 (14H, m), 2,38 (2H, t, J = 7,2 Hz), 2,52 (1H, m), 3,81 (1H, m), 5,33–5,50 (2H, m), 6,08 (1H, d, J = 7,6 Hz), 7,39–7,53 (3H, m), 7,57–7,62 (6H, m).
IR (CHCl3): 3420, 3250, 3008, 2948, 2870, 2660, 2208, 1735 (sh), 1705, 1640, 1500/cm.
[α]D = –21,9 ± 0,6° (CHCl3, c = 1,02, 22°C).
Nr. 1k-5
CDCl3 300 MHz
1,05–2,14 (14H, m), 2,38 (2H, t, J = 7,2 Hz), 2,51 (1H, m), 3,81 (1H, m), 5,34–5,46 (2H, m), 6,07 (1H, d, J = 7,6 Hz), 7,33–7,56 (5H, m).
IR (CHCl3): 3422, 3250, 3010, 2950, 2876, 2664, 2558, 2210, 1735 (sh), 1705, 1645, 1502, 1441, 1410, 1307, 1276/cm.
[α]D = –63,6 ± 1,9° (CHCl3, c = 0,56, 22°C).
Nr. 1k-6
CDCl3 300 MHz
1,04–2,24 (14H, m), 2,36 (2H, t, J = 7,5 Hz), 2,58 (1H, m), 3,88 (1H, m), 5,30–5,43 (2H, m), 6,21 (1H, d, J = 7,2 Hz), 7,41–7,49 (3H, m), 7,73–7,77 (2H, m).
IR (CHCl3): 3447, 3011, 2955, 1708, 1653, 1603, 1578, 1515, 1486, 1457, 1312, 1211, 1164/cm.
[α]D = –60,3° (CHCl3, c = 1,00, 23°C).
Nr. 1k-7
CDCl3 300 MHz
1,04–2,22 (14H, m), 2,36 (2H, t, J = 7,2 Hz), 2,57 (1H, m), 3,87 (1H, m), 5,30–5,44 (2H, m), 6,17 (1H, d, 8,7 Hz), 6,99–7,40 (7H, m), 7,73 (2H, d, J = 7,5 Hz).
IR (CHCl3): 3449, 3013, 2955, 1739, 1708, 1651, 1609, 1588, 1522, 1487, 1243, 1227, 1169/cm.
[α]D = –60,2° (CHCl3, c = 0,92, 23°C).
Nr. 1k-8
CDCl3 300 MHz
1,04–2,25 (14H, m), 2,34 (2H, t, J = 7,5 Hz), 2,56 (1H, m), 3,87 (1H, m), 5,30–5,44 (2H, m), 6,19 (1H, d, J = 7,5 Hz), 6,83–6,94 (6H, m), 7,69 (2H, d, 8,7 Hz).
IR (CHCl3): 3599, 3455, 3012, 2955, 1711, 1644, 1604, 1577, 1524, 1507, 1492, 1290, 1236, 1197, 1170/cm.
[α]D = –47,7° (CHCl3, c = 1,01, 22°C).
Nr. 1k-9
CDCl3 300 MHz
1,04–2,20 (14H, m), 2,31 (3H, s), 2,36 (2H, t, J = 7,2 Hz), 2,56 (1H, m), 3,86 (1H, m), 5,30–5,43 (2H, m), 6,16 (1H, d, J = 7,2 Hz), 7,00–7,11 (6H, m), 7,74 (2H, d, 8,7 Hz).
IR (CHCl3): 3450, 3010, 2955, 1750, 1709, 1651, 1609, 1596, 1523, 1489, 1370, 1247, 1227, 1183/cm.
[α]D = –54,7° (CHCl3, c = 1,01, 22°C).
Nr. 1k-10
CDCl3 300 MHz
1,04–2,22 (14H, m), 2,35 (2H, t, J = 7,2 Hz), 2,56 (1H, m), 3,82 (3H, s), 3,86 (1H, m), 5,30–5,43 (2H, m), 6,17 (1H, d, J = 6,9 Hz), 6,89–7,01 (6H, m), 7,70 (2H, d, 8,7 Hz).
IR (CHCl3): 3023, 2955, 1742, 1708, 1649, 1613, 1602, 1577, 1522, 1507, 1490, 1227, 1210, 1170/cm.
[α]D = –58,1° (CHCl3, c = 1,01, 22°C).
Nr. 1m-1
CDCl3 300 MHz
1,06–2,25 (14H, m), 2,32 (2H, t, J = 7,4 Hz), 2,61 (1H, m), 3,63 (3H, s), 3,91 (1H, m), 5,33–5,47 (2H, m), 6,24 (1H, d, J = 6,9 Hz), 7,35–7,38 (3H, m), 7,53–7,60 (4H, m), 7,75–7,78 (2H, m).
IR (CHCl3): 3438, 3008, 2946, 2875, 2212, 1732, 1650, 1605, 1519, 1496/cm.
[α]D = +76° (CHCl3, c = 1,39, 24°C).
Nr. 1m-2
CDCl3 300 MHz
1,05–2,20 (14H, m), 2,36 (2H, t, J = 6,2 Hz), 2,59 (1H, m), 3,89 (1H, m), 5,29–5,48 (2H, m), 6,26 (1H, d, J = 7,0 Hz), 7,26–7,38 (3H, m), 7,52–7,60 (4H, m), 7,73–7,77 (2H, m).
IR (CHCl3): 3444, 3012, 2952, 2874, 2664, 2214, 1718 (sh), 1708, 1649, 1605, 1520, 1498/cm.
[α]D = +81,4° (CHCl3, c = 1,01, 23°C).
Nr. 1m-3
CDCl3 300 MHz
1,06–2,23 (14H, m), 2,32 (2H, t, J = 7,0 Hz), 2,62 (1H, m), 3,63 (3H, s), 3,93 (1H, m), 5,30–5,50 (2H, m), 6,28 (1H, d, J = 7,0 Hz), 7,38–7,51 (3H, m), 7,58,–7,67 (4H, m), 7,83–7,88 (2H, m).
IR (CHCl3): 3438, 3008, 2948, 2875, 1783 (w), 1727, 1650, 1608, 1580 (w), 1523, 1501, 1482/cm
[α]D = +59° (CHCl3, c = 1,49, 25°C).
Nr. 1m-4
CDCl3 300 MHz
1,08–2,25 (14H, m), 2,36 (2H, t, J = 7,4 Hz), 2,59 (1H, m), 3,91 (1H, m), 5,28–5,48 (3H, m), 6,29 (1H, d, J = 7,4 Hz), 7,38–7,50 (3H, m), 7,61–7,67 (4H, m), 7,81–7,86 (2H, m).
IR (CHCl3): 3436, 3010, 2948, 2868, 1727, 1715 (sh), 1649, 1615 (w), 1524, 1502, 1482, 1372/cm.
[α]D = +72° (CHCl3, c = 0,98, 25°C).
Nr. 1m-5
CDCl3 300 MHz
1,09–2,20 (14H, m), 2,32 (2H, t, J = 7,2 Hz), 2,63 (1H, m), 3,63 (3H, s), 3,92 (1H, m), 5,31–5,51 (2H, m), 6,35 (1H, d, J = 7,0 Hz), 7,51–7,60 (3H, m), 7,92–7,97 (6H, m).
IR (CHCl3): 3436, 3008, 2946, 2875, 1727, 1652, 1608 (w), 1515, 1484/cm.
[α]D = +82° (CHCl3, c = 0,99, 25°C).
Nr. 1m-6
CDCl3 300 MHz
1,09–2,23 (14H, m), 2,37 (2H, t, J = 7,2 Hz), 2,60 (1H, m), 3,92 (1H, m), 5,30–5,49 (2H, m), 6,32 (1H, d, J = 7,4 Hz), 7,51–7,55 (3H, m), 7,85–7,98 (6H, m).
IR (CHCl3): 3436, 3010, 2950, 2875, 2670, 1727, 1715 (sh), 1650, 1605 (w), 1515, 1484/cm.
[α]D = +84° (CHCl3, c = 1,54, 25°C).
Nr. 1m-7
CDCl3 300 MHz
1,03–2,18 (14H, m), 2,32 (2H, t, J = 7,4 Hz), 2,59 (1H, m), 3,64 (3H, s), 3,89 (1H, m), 5,29–5,49 (2H, m), 6,16 (1H, d, J = 7,8 Hz), 6,98–7,06 (4H, m), 7,14–7,20 (1H, m), 7,34–7,41 (2H, m), 7,73–7,78 (2H, m).
IR (CHCl3): 3438, 3008, 2946, 2868, 1727, 1648, 1610, 1586, 1519, 1485/cm.
[α]D = +54° (CHCl3, c = 1,29, 25°C).
Nr. 1m-8
CDCl3 300 MHz
1,06–2,21 (14H, m), 2,36 (2H, t, J = 7,5 Hz), 2,58 (1H, m), 3,88 (1H, m), 5,31–5,46 (2H, m), 6,17 (1H, d, J = 6,9 Hz), 6,99–7,05 (4H, m), 7,15–7,21 (1H, m), 7,36–7,41 (2H, m), 7,72–7,75 (2H, m).
IR (CHCl3): 3436, 3010, 2948, 2868, 2675,1730 (sh), 1709, 1647, 1608, 1586, 1520, 1485/cm.
[α]D = +56° (CHCl3, c = 0,97, 25°C).
Nr. 1m-9
CDCl3 300 MHz
1,05–2,18 (14H, m), 2,29–2,34 (5H, m), 2,59 (1H, m), 3,64 (3H, s), 3,89 (1H, m), 5,32–5,46 (2H, m), 6,16 (1H, d, J = 7,5 Hz), 7,00–7,11 (6H, m), 7,74–7,77 (2H, m).
IR (CHCl3): 3440, 3010, 2946, 2868, 1729, 1649, 1595, 1519, 1488/cm.
[α]D = +47° (CHCl3, c = 0,82, 25°C).
Nr. 1m-10
CDCl3 300 MHz
1,04–2,20 (14H, m), 2,31–2,39 (5H, m), 2,57 (1H, m), 3,87 (1H, m), 5,28–5,47 (2H, m), 6,17 (1H, d, J = 7,0 Hz), 6,99–7,12 (6H, m), 7,72–7,76 (2H, m).
IR (CHCl3): 3674, 3572, 3438, 3010, 2948, 2868, 2626, 1748, 1710, 1648, 1615, 1595, 1520, 1489/cm.
[α]D = +51° (CHCl3, c = 0,91, 25°C).
Nr. 1m-11
CDCl3 300 MHz
1,04–2,16 (14H, m), 2,31 (2H, t, J = 7,2 Hz), 2,59 (1H, m), 3,63 (3H, s), 3,89 (1H, m), 5,29–5,49 (2H, m), 6,24 (1H, d, J = 7,4 Hz), 6,54 (1H, s), 6,83–6,93 (6H, m), 7,69–7,73 (2H, m).
IR (CHCl3): 3674, 3588, 3438, 3296, 3010, 2946, 2868, 1725, 1646, 1603, 1520, 1504, 1489/cm.
[α]D = +51° (CHCl3, c = 0,91, 25°C).
Nr. 1m-12
CDCl3 300 MHz
1,04–2,21 (14H, m), 2,33 (2H, t, J = 8,0 Hz), 2,56 (1H, m), 3,87 (1H, m), 5,28–5,48 (2H, m), 6,23 (1H, d, J = 8,0 Hz), 6,75 (1H, m), 6,87–6,94 (6H, m), 7,66–7,71 (2H, m), 9,63 (1H, br).
IR (CHCl3): 3674, 3582, 3436, 3275, 3010, 2950, 2868, 2675, 1727, 1710 (sh), 1643, 1603, 1522, 1504, 1490/cm.
[α]D = +30° (CHCl3, c = 0,97, 25°C).
Nr. 1m-13
CDCl3 300 MHz
1,01–2,18 (14H, m), 2,31 (2H, t, J = 7,4 Hz), 2,58 (1H, m), 3,63 (3H, s), 3,82 (3H, s), 3,89 (1H, m), 5,29–5,48 (2H, m), 6,14 (1H, d, J = 7,0 Hz), 6,88–7,02 (6H, m), 7,70–7,74 (2H, m).
IR (CHCl3): 3442, 3402, 3004, 2946, 2868, 1727, 1648, 1600, 1518, 1499/cm.
[α]D = +42° (CHCl3, c = 1,82, 26°C).
Nr. 1m-14
CDCl3 300 MHz
1,05–2,21 (14H, m), 2,35 (2H, t, J = 7,2 Hz), 2,55 (1H, m), 3,82 (3H, s), 3,88 (1H, m), 5,27–5,46 (2H, m), 6,16 (1H, d, J = 7,2 Hz), 6,88–7,02 (6H, m), 7,68–7,73 (2H, m).
IR (CHCl3): 3438, 3012, 2948, 2870, 2650, 1730 (sh), 1709, 1647, 1615 (sh), 1601, 1519, 1492/cm.
[α]D = +64° (CHCl3, c = 0,70, 25°C).
Nr. 1m-15
CDCl3 300 MHz
1,05–2,20 (14H, m), 2,29–2,36 (5H, m), 2,62 (1H, m), 3,63 (3H, s), 3,92 (1H, m), 5,30–5,50 (2H, m), 6,25 (1H, d, J = 7,2 Hz), 7,16–7,21 (2H, m), 7,59–7,64 (4H, m), 7,83–7,87 (2H, m).
IR (CHCl3): 3446, 3010, 2946, 2868, 1745 (sh), 1728, 1650, 1615, 1525, 1507, 1486/cm.
[α]D = +65,0° (CHCl3, c = 1,02, 23°C).
Nr. 1m-16
CDCl3 300 MHz
1,08–2,21 (14H, m), 2,34–2,40 (5H, m), 2,59 (1H, m), 3,90 (1H, m), 5,29–5,48 (2H, m), 6,29 (1H, d, J = 7,0 Hz), 7,18 (2H, d, J = 8,6 Hz), 7,58–7,64 (4H, m), 7,83 (2H, d, J = 8,2 Hz).
IR (CHCl3): 3438, 3012, 2948, 2870, 2622, 1749, 1710, 1649, 1610, 1526, 1508, 1487/cm.
[α]D = +66° (CHCl3, c = 1,21, 24°C).
Nr. 1m-17
CDCl3 300 MHz
1,06–2,19 (14H, m), 2,32 (2H, t, J = 7,2 Hz), 2,62 (1H, m), 3,63 (3H, s), 3,93 (1H, m), 5,30–5,50 (2H, m), 6,32 (1H, d, J = 7,6 Hz), 6,41 (1H, s), 6,94 (2H, d, J = 9,0 Hz), 7,47 (2H, d, J = 9,0 Hz), 7,58 (2H, d, J = 8,6 Hz), 7,81 (2H, d, J = 8,6 Hz).
IR (CHCl3): 3580, 3434, 3284, 3010, 2946, 2868, 1726, 1646, 1606, 1528, 1490/cm.
[α]D = +62,4° (CHCl3, c = 1,01, 23°C).
Nr. 1m-18
CDCl3 + CD3OD 300 MHz
1,11–2,18 (14H, m), 2,32 (2H, t, J = 7,4 Hz), 2,59 (1H, m), 3,88 (1H, m), 5,30–5,49 (2H, m), 6,55 (1H, d, J = 7,0 Hz), 6,92 (2H, d, J = 8,6 Hz), 7,47 (2H, d, J = 8,6 Hz), 7,59 (2H, d, J = 8,6 Hz), 7,79 (2H, d, J = 8,2 Hz).
IR (Nujol): 3398, 3175, 2725, 1696, 1635, 1601, 1531, 1510/cm.
[α]D = +99,5° (CH3OH, c = 1,011, 25°C).
Nr. 1m-19
CDCl3 300 MHz
1,05–2,20 (14H, m), 2,32 (2H, t, J = 7,4 Hz), 2,61 (1H, m), 3,63 (3H, s), 3,86 (3H, s), 3,94 (1H, m), 5,30–5,50 (2H, m), 6,24 (1H, d, J = 7,0 Hz), 6,99 (2H, d, J = 8,6 Hz), 7,53–7,63 (4H, m), 7,82 (2H, d, J = 8,6 Hz).
IR (CHCl3): 3440, 3006, 2946, 2875, 1726, 1649, 1606, 1527, 1510, 1489/cm.
[α]D = +68° (CHCl3, c = 0,88, 26°C).
Nr. 1m-20
CDCl3 300 MHz
1,09–2,20 (14H, m), 2,35 (2H, t, J = 7,3 Hz), 2,58 (1H, m), 3,85 (3H, s), 3,89 (1H, m), 5,28–5,48 (2H, m), 6,35 (1H, d, J = 7,2 Hz), 6,98 (2H, d, J = 8,8 Hz), 7,51–7,61 (4H, m), 7,81 (2H, d, J = 8,4 Hz), 8,34 (1H, br).
IR (CHCl3): 3446, 3012, 2952, 2881, 2640, 1730 (sh), 1707, 1647, 1606, 1527, 1510, 1489/cm.
[α]D = +83° (CHCl3, c = 1,00, 25°C).
Nr. 1m-21
CDCl3 300 MHz
1,05–2,14 (14H, m), 2,37 (2H, t, J = 7,2 Hz), 2,51 (1H, m), 3,81 (1H, m), 5,34–5,46 (2H, m), 6,11 (1H, d, J = 7,5 Hz), 7,33–7,48 (3H, m), 7,53–7,55 (2H, m).
IR (CHCl3): 3420, 3250, 3008, 2948, 2870, 2660, 2210, 1735 (sh), 1705, 1645, 1503, 1441, 1409/cm.
[α]D = +59,2 ± 1,0° (CHCl3, c = 1,023, 22°C).
Nr. 1m-22
CDCl3 300 MHz
1,05–2,17 (14H, m), 2,37 (2H, t, J = 7,2 Hz), 2,52 (1H, m), 3,82 (1H, m), 5,32–5,47 (2H, m), 6,20 (1H, d, J = 7,6 Hz), 7,38–7,53 (3H, m), 7,58–7,61 (6H, m), 9,11 (1H, br).
IR (CHCl3): 3420, 3250, 3010, 2984, 2870, 2675, 2208, 1730 (sh), 1705, 1640, 1500, 1406/cm.
[α]D = +57,4° (CHCl3, c = 1,83, 23°C).
Nr. 1m-23
CDCl3 300 MHz
1,05–2,18 (14H, m), 2,31 (2H, t, J = 7,5 Hz), 2,60 (1H, m), 3,63 (3H, s), 3,90 (1H, m), 5,32–5,47 (2H, m), 6,22 (1H, d, J = 6,9 Hz), 7,40–7,49 (3H, m), 7,76–7,79 (2H, m).
IR (CHCl3): 3438, 3008, 2946, 2868, 1727, 1651, 1603, 1585, 1512, 1484/cm.
[α]D = +52° (CHCl3, c = 1,49, 25°C).
Nr. 1m-24
CDCl3 300 MHz
1,05–2,21 (14H, m), 2,36 (2H, t, J = 7,2 Hz), 2,57 (1H, m), 3,89 (1H, m), 5,28–5,47 (2H, m), 6,22 (1H, d, J = 7,0 Hz), 7,39–7,55 (3H, m), 7,73–7,79 (2H, m).
IR (CHCl3): 3676, 3572, 3436, 3010, 2948, 2875, 1730 (sh), 1709, 1650, 1600, 1580, 1514, 1484/cm.
[α]D = +57° (CHCl3, c = 0,97, 26°C).
Nr. 1m-25
CDCl3 300 MHz
1,04–2,18 (14H, m), 2,28–2,35 (5H, m), 2,59 (1H, m), 3,62 (3H, s), 3,88 (1H, m), 5,29–5,49 (2H, m), 6,20 (1H, d, J = 7,2 Hz), 7,15 (2H, d, J = 9,0 Hz), 7,80 (2H, d, J = 8,8 Hz).
IR (CHCl3): 3436, 3010, 2946, 2868, 1752, 1727, 1653, 1602, 1519, 1491/cm.
[α]D = +53° (CHCl3, c = 1,63, 25°C).
Nr. 1m-26
CDCl3 300 MHz
1,05–2,19 (14H, m), 2,32–2,38 (5H, m), 2,56 (1H, m), 3,88 (1H, m), 5,29–5,47 (2H, m), 6,25 (1H, d, J = 7,4 Hz), 7,15 (2H, d, J = 9,0 Hz), 7,78 (2H, d, J = 8,6 Hz).
IR (CHCl3): 3434, 3016, 3006, 2948, 2880, 2622, 1752, 1730 (sh), 1710, 1651, 1605, 1520, 1492/cm.
[α]D = +58° (CHCl3, c = 3,68, 24°C).
Nr. 1m-27
CDCl3 300 MHz
1,05–2,16 (14H, m), 2,30 (2H, t, J = 7,5 Hz), 2,57 (1H, m), 3,62 (3H, s), 3,87 (1H, m), 5,27–5,47 (2H, m), 6,32 (1H, d, J = 7,4 Hz), 6,85 (2H, d, J = 8,6 Hz), 7,62 (2H, d, J = 8,6 Hz), 8,35 (1H, s).
IR (CHCl3): 3580, 3450, 3216, 3010, 2946, 2868, 1726, 1640, 1608, 1584, 1528, 1496/cm.
[α]D = +56,2° (CHCl3, c = 0,713, 23°C).
Nr. 1m-28
CDCl3 200 MHz
1,10–2,25 (14H, m), 2,32 (2H, t, J = 7,2 Hz), 2,55 (1H, br), 3,82–3,93 (1H, m), 5,27–5,47 (2H, m), 6,25 (1H, d, J = 7,4 Hz), 6,86 (2H, d, J = 8,6 Hz), 7,62 (2H, d, J = 8,6 Hz).
IR (CHCl3): 3438, 3242, 2675, 1730 (sh), 1708, 1639, 1607, 1585/cm.
Nr. 1m-29
CDCl3 300 MHz
1,05–2,18 (14H, m), 2,31 (2H, t, J = 7,4 Hz), 2,58 (1H, m), 3,64 (3H, s), 3,85 (3H, s), 3,89 (1H, m), 5,29–5,48 (2H, m), 6,14 (1H, d, J = 6,6 Hz), 6,92 (2H, d, J = 9,0 Hz), 7,74 (2H, d, J = 9,0 Hz).
IR (CHCl3): 3445, 3008, 2946, 2868, 1727, 1646, 1606, 1578, 1523, 1493/cm.
[α]D = +53° (CHCl3, c = 2,03, 24°C).
Nr. 1m-30
CDCl3 300 MHz
1,04–2,21 (14H, m), 2,36 (2H, t, J = 7,3 Hz), 2,56 (1H, m), 3,85 (3H, s), 3,88 (1H, m), 5,27–5,46 (2H, m), 6,15 (1H, d, J = 7,2 Hz), 6,92 (2H, d, J = 8,6 Hz), 7,73 (2H, d, J = 8,6 Hz) IR (CHCl3): 3440, 3010, 2950, 2870, 2645, 1727, 1710 (sh), 1646, 1606, 1575, 1524, 1494/cm.
[α]D = +62° (CHCl3, c = 1,10, 24°C).
Nr. 1m-31
CDCl3 + CD3OD 300 MHz
1,16–2,20 (14H, m), 2,31 (2H, t, J = 7,2 Hz), 2,59 (1H, m), 3,85 (1H, m), 5,31–5,51 (2H, m), 7,13–7,21 (1H, m), 7,31–7,42 (2H, m), 7,68–7,93 (6H, m).
IR (Nujol): 3344, 3175, 2715, 2675, 1699, 1631, 1566/cm.
[α]D = +67° (CH3OH, c = 1,01, 24°C).
Nr. 1m-32
CDCl3 200 MHz
1,09–2,23 (14H, m), 2,33 (2H, t, J = 7,1 Hz), 2,57 (1H, br), 3,40–3,93 (9H, m), 4,41 (1H, br), 5,29–5,48 (2H, m), 6,44 (1H, d, J = 7,4 Hz), 7,43 (2H, d, J = 8,2 Hz), 7,80 (2H, d, J = 7,8 Hz).
IR (CHCl3): 3434, 3354, 1726, 1720 (sh), 1660 (sh), 1626/cm.
Nr. 1m-33
CDCl3 200 MHz
1,14–2,25 (14H, m), 2,37 (2H, t, J = 7,3 Hz), 2,64 (1H, br), 3,93–4,01 (1H, m), 5,30–5,51 (2H, m), 6,47 (1H, d, J = 7,4 Hz), 7,63–7,74 (2H, m), 7,79 (2H, s), 7,89–7,93 (1H, m), 8,00 (1H, dd, J = 2,3, 1,0 Hz), 8,30 (1H, d, J = 1,0 Hz), 8,65–8,73 (2H, m).
IR (CHCl3): 3450, 2675, 1728, 1707, 1649, 1528, 1509/cm.
[α]D = +82,8 ± 1,2° (CHCl3, c = 1,01, 23°C).
Nr. 2a-1
[α]D = +69,0° (MeOH, c = 1,01, 25°C).
Nr. 2a-2
CDCl3 300 MHz
0,99 (1H, d, J = 10,2 Hz), 1,15 und 1,24 (jeweils 3H, jeweils s), 1,50–2,50 (14H, m), 4,30 (1H, m), 5,35–5,52 (2H, m), 6,32 (1H, d, 8,7 Hz), 7,36–7,49 (3H, m), 7,58–7,62 (2H, m), 7,66 und 7,80 (jeweils 2H, jeweils d, 8,7 Hz).
IR (CHCl3): 3116, 3014, 2925, 2870, 2663, 1708, 1651, 1610, 1524, 1504, 1484, 1472/cm.
[α]D = +64,1° (MeOH, c = 1,02, 25°C).
Nr. 2a-3
[α]D = +76,6° (MeOH, c = 1,18, 26°C).
Nr. 2a-4
CDCl3 300 MHz
0,99 (1H, d, J = 10,2 Hz), 1,15 und 1,25 (jeweils 3H, jeweils s), 1,64–2,51 (14H, m), 4,31 (1H, m), 5,36–5,53 (2H, m), 6,33 (1H, d, J = 8,4 Hz), 7,50–7,56 (3H, m), 7,85–7,98 (6H, m).
IR (CHCl3): 3515, 3452, 3014, 2925, 2870, 1740, 1708, 1654, 1517, 1486, 1470/cm.
[α]D = +79,5° (MeOH, c = 1,18, 22°C).
Nr. 2a-5
CD3OD 300 MHz
0,98 (1H, d, J = 9,9 Hz), 1,18 und 1,25 (jeweils 3H, jeweils s), 1,56–1,71 (3H, m), 1,98–2,40 (11H, m), 4,17 (1H, m), 5,41–5,52 (2H, m), 7,52–7,61 (3H, m), 7,91–8,01 (6H, m),
IR (KBr): 3416, 3063, 2983, 2921, 2869, 1704, 1643, 1566, 1518, 1488, 1408/cm.
[α]D = +62,0° (MeOH, c = 1,00, 25°C).
Nr. 2a-6
[α]D = +64,1° (MeOH, c = 1,01, 25°C).
Nr. 2a-7
[α]D = +65,3° (MeOH, c = 0,99, 25°C).
Nr. 2a-8
[α]D = +74,0° (MeOH, c = 1,01, 25°C).
Nr. 2a-9
[α]D = +71,0° (MeOH, c = 1,10, 25°C).
Nr. 2a-10
[α]D = +74,7° (MeOH, c = 1,00, 25°C).
Nr. 2a-11
[α]D = +72,1° (MeOH, c = 1,00, 25°C).
Nr. 2a-12
[α]D = +53,1° (CHCl3, c = 1,01, 26°C).
Schmp. 155,0–156,0°C.
Nr. 2a-13
CDCl3 300 MHz
0,98 (1H, d, J = 10,2 Hz), 1,18 und 1,25 (jeweils 3H, jeweils s), 1,63–2,40 (14H, m), 4,30 (1H, m), 5,46–5,58 (2H, m), 6,44 (1H, d, J = 8,4 Hz), 7,49 und 7,77 (jeweils 2H, jeweils d, 8,7 Hz), 7,54 (1H, s).
IR (CHCl3): 3689, 3378, 3028, 3014, 2924, 1713, 1652, 1602, 1522, 1496/cm.
[α]D = +78,3° (MeOH, c = 0,84, 25°C).
Schmp. 205,0–206,0°C.
Nr. 2a-14
[α]D = +72,5° (MeOH, c = 1,07, 25°C).
Nr. 2a-15
CDCl3 300 MHz
0,99 (1H, d, J = 9,9 Hz), 1,14 und 1,24 (jeweils 3H, jeweils s), 1,55–2,44 (14H, m), 4,27 (1H, m), 5,30–5,50 (2H, m), 6,29 (1H, d, J = 9,0 Hz), 7,11 und 7,20 (jeweils 1H, jeweils d, J = 16,2 Hz), 7,29–7,55 (5H, m), 7,57 und 7,72 (jeweils 2H, jeweils d, 8,7 Hz).
IR (CHCl3): 3453, 3083, 3022, 3013, 2925, 2870, 1708, 1650, 1607, 1560, 1522, 1496/cm.
[α]D = +72,3° (MeOH, c = 1,00, 27°C).
Schmp. 115,0–117,0°C.
Nr. 2a-16
CDCl3 300 MHz
0,92 (1H, d, J = 10,2 Hz), 1,11 und 1,23 (jeweils 3H, jeweils s), 1,50–2,48 (14H, m), 3,62 (3H, s), 4,29 (1H, m), 5,30–5,50 (2H, m), 6,20 (1H, d, 8,7 Hz), 6,59 und 6,68 (jeweils 1H, jeweils d, J = 12,3 Hz), 7,23 (5H, s), 7,29 und 7,59 (jeweils 2H, jeweils d, J = 8,1 Hz).
IR (CHCl3): 3453, 3024, 3016, 2924, 2870, 1730, 1651, 1607, 1520, 1495/cm.
[α]D = +56,8° (MeOH, c = 1,04, 24°C).
Nr. 2a-17
CDCl3 300 MHz
0,97 (1H, d, J = 10,2 Hz), 1,11 und 1,23 (jeweils 3H, jeweils s), 1,50–2,38 (14H, m), 4,26 (1H, m), 5,30–5,50 (2H, m), 6,23 (1H, d, J = 8,4 Hz), 6,59 und 6,70 (jeweils 1H, jeweils d, J = 12,3 Hz), 7,23 (5H, s), 7,30 und 7,57 (jeweils 2H, jeweils d, 8,7 Hz).
IR (CHCl3): 3452, 3081, 3019, 3014, 2925, 2870, 2665, 1708, 1650, 1607, 1521, 1495/cm.
[α]D = +61,6° (MeOH, c = 1,00, 27°C).
Nr. 2a-18
CDCl3 300 MHz
0,97 (1H, d, J = 10,2 Hz), 1,11 und 1,23 (jeweils 3H, jeweils s), 1,50–2,50 (14H, m), 3,61 (3H, s), 4,31 (1H, m), 5,35–5,51 (2H, m), 6,33 (1H, d, J = 8,4 Hz), 7,48–7,64 (4H, m), 7,79–7,83 (2H, m), 7,91 (1H, dt, J = 1,5 und 7,8 Hz), 8,01 (1H, dt, J = 1,5 und 7,8 Hz), 8,13 (1H, t, J = 1,5 Hz).
IR (CHCl3): 3450, 3026, 3013, 2925, 2870, 1730, 1659, 1600, 1510/cm.
[α]D = +56,0° (MeOH, c = 1,01, 25°C).
Nr. 2a-19
CDCl3 300 MHz
0,95 (1H, d, J = 9,9 Hz), 1,14 und 1,21 (jeweils 3H, jeweils s), 1,53–2,60 (14H, m), 4,25 (1H, m), 5,35–5,64 (2H, m), 7,21 (1H, d, J = 7,8 Hz), 7,49–7,68 (4H, m), 7,76–7,84 (3H, m), 8,25 (1H, m), 8,43 (1H, m).
IR (CHCl3): 3382, 3196, 3025, 3015, 2925, 2870, 1725, 1652, 1599, 1577, 1521/cm.
[α]D = +55,9° (MeOH, c = 1,00, 25°C).
Nr. 2a-20
CDCl3 300 MHz
0,98 (1H, d, J = 10,2 Hz), 1,13 und 1,24 (jeweils 3H, jeweils s), 1,50–2,50 (14H, m), 3,62 (3H, s), 4,31 (1H, m), 5,35–5,51 (2H, m), 6,24 (1H, d, J = 8,4 Hz), 7,40–7,52 (3H, m), 7,71–7,76 (2H, m).
IR (CHCl3): 3453, 3025, 3013, 2925, 2870, 1730, 1753, 1579, 1514, 1486/cm.
[α]D = +61,2° (MeOH, c = 1,04, 25°C).
Nr. 2a-21
CDCl3 300 MHz
0,98 (1H, d, J = 10,2 Hz), 1,13 und 1,23 (jeweils 3H, jeweils s), 1,52–2,50 (14H, m), 4,28 (1H, m), 5,34–5,51 (2H, m), 6,27 (1H, d, 8,7 Hz), 7,41–7,53 (3H, m), 7,71–7,74 (2H, m).
IR (CHCl3): 3452, 3063, 3027, 3014, 2925, 2871, 1708, 1652, 1578, 1515, 1486/cm.
[α]D = +62,0° (MeOH, c = 1,01, 27°C).
Nr. 2a-22
d6-DMSO 300 MHz
0,86 (1H, d, J = 9,9 Hz), 1,10 und 1,16 (jeweils 3H, jeweils s), 1,42–1,52 (3H, m), 1,85–2,46 (11H, m), 3,98 (1H, m), 5,32–5,43 (2H, m), 7,41 (3H, m), 7,88 (2H, d, J = 6,6 Hz), 8,19 (1H, d, J = 6,6 Hz).
IR (KBr): 3367, 3060, 2984, 2922, 2868, 1634, 1563, 1529, 1487/cm.
[α]D = +47,7° (MeOH, c = 1,00, 25°C).
Nr. 2a-23
[α]D = +62,7° (MeOH, c = 1,01, 27°C).
Nr. 2a-24
CDCl3 300 MHz
0,99 (1H, d, J = 10,2 Hz), 1,14 und 1,25 (jeweils 3H, jeweils s), 1,52–2,50 (14H, m), 4,31 (1H, m), 5,36–5,52 (2H, m), 6,34 (1H, d, J = 8,4 Hz), 7,47–7,52 (2H, m), 7,59–7,64 (1H, m), 7,78–7,83 (6H, m).
IR (CHCl3): 3449, 3027, 3013, 2925, 2869, 1708, 1656, 1599, 1518, 1493/cm.
[α]D = +63,1° (MeOH, c = 1,00, 25°C).
Nr. 2a-25
[α]D = +35,1° (MeOH, c = 1,00, 25°C).
Nr. 2a-26
[α]D = +35,5° (MeOH, c = 1,02, 25°C).
Nr. 2a-27
CDCl3 300 MHz
0,97 (1H, d, J = 10,2 Hz), 1,12 und 1,23 (jeweils 3H, jeweils s), 1,52–2,50 (14H, m), 3,63 (3H, s), 4,29 (1H, m), 5,36–5,51 (2H, m), 6,18 (1H, d, J = 8,4 Hz), 7,01 und 7,71 (jeweils 2H, jeweils d, 8,7 Hz,), 6,98–7,05 (2H, m), 7,16 (1H, t, J = 7,5 Hz), 7,34–7,41 (2H, m).
IR (CHCl3): 3455, 3024, 3016, 2924, 2870, 1730, 1651, 1588, 1520, 1487/cm.
[α]D = +56,4° (MeOH, c = 1,01, 25°C).
Nr. 2a-28
CDCl3 300 MHz
0,98 (1H, d, J = 10,2 Hz), 1,12 und 1,23 (jeweils 3H, jeweils s), 1,52–2,50 (14H, m), 4,26 (1H, m), 5,34–5,51 (2H, m), 6,20 (1H, d, J = 9,0 Hz), 7,01 und 7,70 (jeweils 2H, jeweils d, J = 9,0 Hz,), 6,98–7,15 (2H, m), 7,17 (1H, t, J = 7,5 Hz), 7,34–7,40 (2H, m).
IR (CHCl3): 3454, 3031, 3018, 2925, 2870, 1708, 1650, 1588, 1523, 1487/cm.
[α]D = +56,2° (MeOH, c = 1,00, 25°C).
Nr. 2a-29
[α]D = +53,0° (MeOH, c = 1,03, 25°C).
Nr. 2a-30
CDCl3 300 MHz
0,97 (1H, d, J = 10,2 Hz), 1,10 und 1,23 (jeweils 3H, jeweils s), 1,52–2,50 (14H, m), 4,25 (1H, m), 5,30–5,50 (2H, m), 6,23 (1H, d, 8,7 Hz), 6,36 (1H, s), 7,26–7,39 (10H, m), 7,60 und 7,68 (jeweils 2H, jeweils d, J = 8,4 Hz,).
IR (CHCl3): 3451, 3088, 3064, 3029, 3014, 2925, 2869, 1707, 1652, 1522, 1495/cm.
[α]D = +54,2° (MeOH, c = 1,00, 25°C).
Nr. 2a-31
CDCl3 300 MHz
0,98 (1H, d, J = 10,2 Hz), 1,14 und 1,24 (jeweils 3H, jeweils s), 1,50–2,50 (14H, m), 3,63 (3H, s), 4,31 (1H, m), 5,30–5,50 (2H, m), 6,26 (1H, d, J = 8,4 Hz), 6,90 (1H, t, J = 7,4 Hz), 7,13 (1H, d, 8,7 Hz), 7,29 (2H, t, J = 8,0 Hz), 7,67–7,75 (5H, m), 7,82 (1H, s).
IR (Nujol): 3380, 3244, 1723, 1638, 1601, 1578, 1535, 1495/cm.
[α]D = +73,6° (MeOH, c = 0,50, 26°C).
Schmp. 133,0–134,0°C.
Nr. 2a-32
[α]D = +56,1° (MeOH, c = 1,02, 26°C).
Nr. 2a-33
CDCl3 300 MHz
0,95 (1H, d, J = 10,2 Hz), 1,10 und 1,21 (jeweils 3H, jeweils s), 1,50–2,50 (14H, m), 4,25 (1H, m), 5,13 (2H, s), 5,30–5,70 (3H, m), 6,41 (1H, d, J = 8,2 Hz), 6,89 (1H, s); 7,09 (1H, s), 7,17 und 7,72 (jeweils 2H, jeweils d, J = 8,2 Hz), 7,62 (1H, s).
IR (CHCl3): 3450, 3125, 3031, 3013, 2925, 2870, 2467, 1917, 1708, 1654, 1615, 1575, 1523, 1497/cm.
[α]D = +55,2° (MeOH, c = 1,01, 26°C).
Nr. 2a-34
[α]D = +72,9° (MeOH, c = 1,03, 25°C).
Nr. 2a-35
CDCl3 300 MHz
0,98 (1H, d, J = 10,2 Hz), 1,13 und 1,24 (jeweils 3H, jeweils s), 1,52–2,48 (14H, m), 4,28 (1H, m), 5,35–5,51 (2H, m), 6,28 (1H, d, 8,7 Hz), 7,34–7,37 (3H, m), 7,52–7,55 (2H, m), 7,58 und 7,71 (jeweils 2H, jeweils d, 8,7 Hz).
IR (CHCl3): 3515, 3452, 3030, 3012, 2925, 2870, 1739, 1708, 1652, 1607, 1555, 1521, 1497/cm.
[α]D = +74,3° (MeOH, c = 1,01, 25°C).
Nr. 2a-36
[α]D = +23,4° (MeOH, c = 1,07, 25°C).
Nr. 2a-37
CDCl3 300 MHz
0,83 (1H, d, J = 10,5 Hz), 0,95 und 1,18 (jeweils 3H, jeweils s), 1,44–2,46 (14H, m), 3,92 (1H, m), 5,34–5,52 (3H, m), 7,26–7,54 (9H, m), 7,62 (1H, s).
IR (CHCl3): 3432, 3310, 3189, 3023, 3014, 2924, 2870, 1704, 1610, 1594, 1523, 1487/cm.
[α]D = +25,3° (MeOH, c = 1,00, 26°C).
Nr. 2a-38
[α]D = +70,9° (MeOH, c = 1,02, 25°C).
Nr. 2a-39
[α]D = +70,6° (MeOH, c = 1,01, 25°C).
Nr. 2a-40
[α]D = +74,7° (MeOH, c = 1,00, 25°C).
Nr. 2a-41
[α]D = +72,1° (MeOH, c = 1,01, 24°C).
Nr. 2a-42
[α]D = +69,2° (MeOH, c = 1,00, 25°C).
Nr. 2a-43
[α]D = +70,8° (MeOH, c = 1,00, 25°C).
Nr. 2a-44
[α]D = +60,4° (MeOH, c = 1,00, 26°C).
Nr. 2a-45
CDCl3 300 MHz
0,97 (1H, d, J = 9,9 Hz), 1,13 und 1,23 (jeweils 3H, jeweils s), 1,55–2,52 (14H, m), 4,29 (1H, m), 5,34–5,54 (2H, m), 6,33 (1H, d, J = 9,0 Hz), 7,10 (1H, t, J = 7,4 Hz), 7,34 (2H, t, J = 7,4 Hz), 7,52 (2H, m), 7,68 und 7,75 (jeweils 2H, jeweils d, J = 8,4 Hz), 7,80 (1H, s), 8,10 (1H, s), 10,09 (1H, s).
IR (CHCl3): 3393, 3195, 3093, 3033, 3013, 2925, 2870, 1698, 1656, 1598, 1537, 1498/cm.
[α]D = +59,4° (MeOH, c = 1,01, 24°C).
Nr. 2a-46
[α]D = +63,5° (MeOH, c = 1,00, 25°C).
Nr. 2a-47
CDCl3 300 MHz
0,97 (1H, d, J = 9,9 Hz), 1,12 und 1,23 (jeweils 3H, jeweils s), 1,54–2,48 (14H, m), 4,29 (1H, m), 5,35–5,52 (2H, m), 6,32 (1H, d, 8,7 Hz), 7,26 (1H, m), 7,41 (2H, t, J = 7,8 Hz), 7,64 (2H, d, J = 7,5 Hz), 7,73 und 7,77 (jeweils 2H, jeweils d, J = 8,4 Hz), 7,95 (1H, s), 9,20 (1H, s), 10,38 (1H, s).
IR (CHCl3): 3450, 3339, 3003, 2992, 2925, 2870, 1706, 1653, 1596, 1523, 1495/cm.
[α]D = +63,3° (MeOH, c = 1,00, 25°C).
Nr. 2a-48
[α]D = +63,8° (MeOH, c = 1,00, 24°C).
Nr. 2a-49
CDCl3 300 MHz
1,00 (1H, d, J = 10,5 Hz), 1,17 und 1,26 (jeweils 3H, jeweils s), 1,55–2,52 (14H, m), 4,34 (1H, m), 5,36–5,54 (2H, m), 6,35 (1H, d, J = 9,0 Hz), 7,50–7,62 (3H, m), 7,90 und 8,33 (jeweils 2H, jeweils d, J = 8,4 Hz), 8,21 (2H, m)
IR (CHCl3): 3451, 3029, 3022, 3016, 2925, 2870, 1708, 1655, 1542, 1508, 1498, 1471, 1459/cm.
[α]D = +63,5° (MeOH, c = 1,02, 25°C).
Schmp. 135,0–137,0°C.
Nr. 2a-50
[α]D = +68,9° (MeOH, c = 1,01, 24°C).
Nr. 2a-51
d6-DMSO 300 MHz
0,87 (1H, d, J = 9,9 Hz), 1,10 und 1,17 (jeweils 3H, jeweils s), 1,40–1,60 (3H, m), 1,90–2,40 (11H, m), 3,98 (1H, m), 5,35–5,46 (2H, m), 7,64 (1H, s), 7,65 und 7,91 (jeweils 2H, jeweils d, 8,7 Hz), 8,06 (1H, d, J = 6,0 Hz), 9,32 (1H, br).
IR (KBr): 3385, 2962, 1734, 1707, 1632, 1529, 1498/cm.
[α]D = +68,4° (MeOH, c = 1,01, 24°C).
Nr. 2a-52
[α]D = +76,2° (MeOH, c = 1,01, 24°C).
Nr. 2a-53
[α]D = +73,9° (MeOH, c = 1,02, 24°C).
Nr. 2a-54
[α]D = +68,1° (MeOH, c = 1,00, 24°C).
Nr. 2a-55
[α]D = +67,8° (MeOH, c = 1,00, 24°C).
Nr. 2a-56
[α]D = +65,4° (MeOH, c = 1,03, 25°C).
Nr. 2a-57
[α]D = +63,4° (MeOH, c = 1,01, 24°C).
Nr. 2a-58
[α]D = +66,6° (MeOH, c = 1,01, 24°C).
Nr. 2a-59
[α]D = +65,5° (MeOH, c = 1,00, 24°C).
Nr. 2a-60
[α]D = +60,9° (MeOH, c = 1,02, 25°C).
Nr. 2a-61
CDCl3 300 MHz
0,97 (1H, d, J = 10,0 Hz), 1,10 und 1,22 (jeweils 3H, jeweils s), 1,50–2,50 (14H, m), 4,26 (1H, m), 5,30–5,54 (2H, m), 6,28 (1H, d, J = 8,6 Hz), 6,60 und 6,82 (jeweils 1H, jeweils d, J = 12,4 Hz), 7,12 (2H, d, J = 6,0 Hz), 7,25 und 7,62 (jeweils 2H, jeweils d, J = 8,6 Hz), 8,47 (2H, d, J = 6,0 Hz).
IR (CHCl3): 3452, 3027, 3019, 3013, 2925, 2870, 2980, 1708, 1651, 1606, 1520, 1494/cm.
[α]D = +61,6° (MeOH, c = 1,01, 25°C).
Nr. 2a-62
[α]D = +72,0° (MeOH, c = 0,93, 25°C).
Nr. 2a-63
CDCl3 300 MHz
0,99 (1H, d, J = 10,2 Hz), 1,14 und 1,24 (jeweils 3H, jeweils s), 1,50–2,50 (14H, m), 4,29 (1H, m), 5,36–5,55 (2H, m), 6,35 (1H, d, J = 9,1 Hz), 7,04 und 7,27 (jeweils 1H, jeweils d, J = 16,5 Hz), 7,37 (2H, d, J = 6,6 Hz), 7,56 und 7,76 (jeweils 2H, jeweils d, J = 8,4 Hz), 8,57 (2H, d, J = 6,6 Hz).
IR (CHCl3): 3452, 3024, 3018, 3014, 2925, 2870, 2470, 1933, 1708, 1652, 1605, 1521, 1496/cm.
[α]D = +69,2° (MeOH, c = 1,01, 25°C).
Nr. 2a-64
[α]D = +56,9° (MeOH, c = 1,24, 25°C).
Nr. 2a-65
CDCl3 300 MHz
0,98 (1H, d, J = 10,5 Hz), 1,12 und 1,23 (jeweils 3H, jeweils s), 1,54–2,46 (14H, m), 4,27 (1H, m), 5,23 (2H, s), 5,34–5,52 (2H, m), 6,26 (1H, d, J = 8,4 Hz), 7,32–7,45 (5H, m), 7,64 und 7,71 (jeweils 2H, jeweils d, J = 8,4 Hz), 8,15 (1H, s).
IR (CHCl3): 3452, 3088, 3065, 3032, 3013, 2925, 2870, 1708, 1653, 1611, 1559, 1522, 1496/cm.
[α]D = +61,0° (MeOH, c = 0,91, 25°C).
Nr. 2a-66
[α]D = +76,0° (MeOH, c = 1,01, 25°C).
Nr. 2a-67
CDCl3 300 MHz
0,98 (1H, d, J = 10,4 Hz), 1,14 und 1,24 (jeweils 3H, jeweils s), 1,54–2,46 (14H, m), 4,28 (1H, m), 5,32–5,53 (2H, m), 6,27 (1H, d, J = 8,6 Hz), 6,92–7,31 (jeweils 1H, jeweils d, J = 16,4 Hz), 7,02 (1H, dd, J = 5,8 und 3,6 Hz), 7,12 (1H, d, J = 3,6 Hz), 7,24 (1H, d, J = 5,8 Hz), 7,51 und 7,70 (jeweils 2H, jeweils d, J = 8,4 Hz).
IR (CHCl3): 3453, 3029, 3013, 2925, 2870, 1739, 1650, 1604, 1524, 1515, 1494/cm.
[α]D = +76,2° (MeOH, c = 1,00, 24°C).
Schmp. 104,0–106,0°C.
Nr. 2a-68
[α]D = +57,7° (MeOH, c = 1,01, 25°C).
Nr. 2a-69
CDCl3 300 MHz
0,99 (1H, d, J = 10,2 Hz), 1,14 und 1,24 (jeweils 3H, jeweils s), 1,54–2,48 (14H, m), 4,28 (1H, m), 5,34–5,53 (2H, m), 6,29 (1H, d, J = 9,0 Hz), 6,54–6,74 (jeweils 1H, jeweils d, J = 12,0 Hz), 7,02 (1H, dd, J = 4,8 und 3,3 Hz), 6,97 (1H, dd, J = 3,3 und 1,2 Hz), 7,13 (1H, dd, J = 4,8 und 1,2 Hz), 7,44 und 7,70 (jeweils 2H, jeweils d, 8,7 Hz).
IR (CHCl3): 3453, 3025, 3010, 2925, 2870, 1708, 1650, 1607, 1559, 1523, 1493/cm.
[α]D = +58,4° (MeOH, c = 1,00, 25°C).
Nr. 2a-70
[α]D = +48,6° (MeOH, c = 1,00, 25°C).
Nr. 2a-71
CDCl3 300 MHz
0,98 (1H, d, J = 10,2 Hz), 1,12 und 1,23 (jeweils 3H, jeweils s), 1,52–2,46 (14H, m), 2,31 (3H, s), 4,26 (1H, m), 5,33–5,52 (2H, m), 6,20 (1H, d, J = 9,3 Hz), 7,02–7,11 (6H, m), 7,70 (2H, d, J = 9,0 Hz).
IR (CHCl3): 3460, 3031, 3022, 3011, 2925, 2870, 1750, 1708, 1650, 1608, 1597, 1523, 1490/cm.
[α]D = +48,9° (MeOH, c = 1,01, 25°C).
Nr. 2a-72
[α]D = +51,2° (MeOH, c = 1,02, 25°C).
Nr. 2a-73
CDCl3 300 MHz
0,97 (1H, d, J = 9,9 Hz), 1,11 und 1,23 (jeweils 3H, jeweils s), 1,54–2,48 (14H, m), 4,27 (1H, m), 5,32–5,52 (2H, m), 6,24 (1H, d, J = 9,0 Hz), 6,83–6,94 (6H, m), 7,65 (2H, d, J = 9,0 Hz).
IR (CHCl3): 3598, 3451, 3199, 3033, 3012, 2925, 2870, 1708, 1642, 1604, 1524, 1507, 1491/cm.
[α]D = +52,2° (MeOH, c = 1,01, 25°C).
Nr. 2a-74
[α]D = +51,5° (MeOH, c = 0,92, 25°C).
Nr. 2a-75
CDCl3 300 MHz
0,97 (1H, d, J = 10,2 Hz), 1,11 und 1,23 (jeweils 3H, jeweils s), 1,55–2,46 (14H, m), 3,82 (3H, s), 4,25 (1H, m), 5,32–5,52 (2H, m), 6,19 (1H, d, 8,7 Hz), 6,89–7,01 (6H, m), 7,65–7,68 (2H, m).
IR (CHCl3): 3450, 3025, 3008, 2925, 2870, 2837, 1741, 1649, 1612, 1521, 1505, 1490/cm.
[α]D = +51,1° (MeOH, c = 1,00, 25°C).
Nr. 2a-76
[α]D = +60,4° (MeOH, c = 0,98, 25°C).
Nr. 2a-77
CDCl3 300 MHz
0,99 (1H, d, J = 10,5 Hz), 1,15 und 1,24 (jeweils 3H, jeweils s), 1,54–2,48 (14H, m), 2,34 (3H, s), 4,29 (1H, m), 5,32–5,54 (2H, m), 6,32 (1H, d, J = 8,4 Hz), 7,19 und 7,60 (jeweils 2H, jeweils d, J = 8,4 Hz), 7,63 und 7,79 (jeweils 2H, jeweils d, J = 8,4 Hz).
IR (CHCl3): 3452, 3027, 3012, 2925, 2870, 1751, 1709, 1651, 1611, 1560, 1527, 1509, 1489/cm.
[α]D = +61,2° (MeOH, c = 1,00, 25°C).
Nr. 2a-78
[α]D = +67,4° (MeOH, c = 1,01, 25°C).
Nr. 2a-79
CDCl3 300 MHz
0,99 (1H, d, J = 10,2 Hz), 1,15 und 1,24 (jeweils 3H, jeweils s), 1,54–2,54 (14H, m), 4,31 (1H, m), 5,32–5,54 (2H, m), 6,36 (1H, d, J = 8,2 Hz), 6,93 und 7,48 (jeweils 2H, jeweils d, J = 8,6 Hz), 7,59 und 7,75 (jeweils 2H, jeweils d, J = 8,4 Hz),
IR (CHCl3): 3593, 3448, 3192, 3030, 3010, 2925, 2870, 1708, 1644, 1608, 1591, 1559, 1530, 1516, 1491/cm.
[α]D = +65,8° (MeOH, c = 1,01, 25°C).
Nr. 2a-80
[α]D = +66,9° (MeOH, c = 1,01, 25°C).
Nr. 2a-81
CDCl3 300 MHz
0,99 (1H, d, J = 10,5 Hz), 1,15 und 1,24 (jeweils 3H, jeweils s), 1,54–2,48 (14H, m), 3,86 (3H, s), 4,29 (1H, m), 5,34–5,52 (2H, m), 6,20 (1H, d, 8,7 Hz), 6,99 und 7,55 (jeweils 2H, jeweils d, J = 9,0 Hz), 7,61 und 7,77 (jeweils 2H, jeweils d, 8,7 Hz).
IR (CHCl3): 3450, 3009, 2925, 2870, 2838, 1740, 1708, 1650, 1608, 1557, 1528, 1512, 1491/cm.
[α]D = +66,2° (MeOH, c = 1,01, 25°C).
Nr. 2a-82
[α]D = +57,7° (MeOH, c = 1,02, 24°C).
Nr. 2a-83
CDCl3 300 MHz
0,97 (1H, d, J = 10,2 Hz), 1,12 and, 1,23 (jeweils 3H, jeweils s), 1,54–2,48 (14H, m), 2,33 (3H, s), 4,26 (1H, m), 5,32–5,52 (2H, m), 6,25 (1H, d, 8,7 Hz), 7,16 und 7,75 (jeweils 2H, jeweils d, 8,7 Hz).
IR (CHCl3): 3452, 3030, 3022, 3012, 2925, 2870, 1754, 1709, 1654, 1604, 1585, 1522, 1493/cm.
[α]D = +57,4° (MeOH, c = 1,01, 24°C).
Nr. 2a-84
[α]D = +57,8° (MeOH, c = 1,01, 24°C).
Nr. 2a-85
CDCl3 300 MHz
0,95 (1H, d, J = 10,2 Hz), 1,12 und 1,22 (jeweils 3H, jeweils s), 1,54–2,48 (14H, m), 4,25 (1H, m), 5,32–5,52 (2H, m), 6,28 (1H, d, 8,7 Hz), 6,87 und 7,57 (jeweils 2H, jeweils d, J = 9,0 Hz).
IR (CHCl3): 3590, 3450, 3166, 3019, 3012, 2925, 2871, 1708, 1637, 1608, 1583, 1531, 1498/cm.
[α]D = +56,0° (MeOH, c = 1,01, 24°C).
Nr. 2a-86
[α]D = +59,3° (MeOH, c = 1,01, 22°C).
Nr. 2a-87
CDCl3 300 MHz
0,98 (1H, d, J = 10,0 Hz), 1,13 und 1,23 (jeweils 3H, jeweils s), 1,54–2,48 (14H, m), 3,85 (3H, s), 4,25 (1H, m), 5,32–5,53 (2H, m), 6,19 (1H, d, J = 8,8 Hz), 6,93 und 7,69 (jeweils 2H, jeweils d, J = 9,0 Hz).
IR (CHCl3): 3450, 3030, 3017, 3012, 2925, 2870, 2840, 1740, 1708, 1647, 1606, 1575, 1525, 1496/cm.
[α]D = +58,2° (MeOH, c = 0,99, 22°C).
Nr. 2a-88
[α]D = +50,9° (MeOH, c = 1,02, 25°C).
Nr. 2a-89
CDCl3 300 MHz
0,99 (1H, d, J = 10,2 Hz), 1,18 und 1,26 (jeweils 3H, jeweils s), 1,56–2,48 (14H, m), 4,29 (1H, m), 5,36–5,54 (2H, m), 7,03 (1H, d, 8,7 Hz), 7,21 (1H, s), 7,43 (2H, m), 7,74 (1H, ddd, J = 1,8, 6,9 und 8,7 Hz), 8,22 (1H, dd, J = 1,8 und 8,1 Hz).
IR (CHCl3): 3443, 3087, 3023, 3014, 2925, 2870, 1708, 1685, 1658, 1630, 1517, 1466/cm.
[α]D = +57,1° (MeOH, c = 1,01, 22°C).
Schmp. 117,0–118,0°C.
Nr. 2a-90
[α]D = +54,1° (MeOH, c = 1,01, 22°C).
Nr. 2a-91
CDCl3 300 MHz
0,97 (1H, d, J = 10,2 Hz), 1,13 und 1,23 (jeweils 3H, jeweils s), 1,52–2,46 (14H, m), 4,24 (1H, m), 5,34–5,52 (2H, m), 6,49–6,53 (12H, m), 7,11 (1H, dd, J = 0,9 und 3,6 Hz), 7,44 (1H, dd, J = 0,9 und 1,8 Hz).
IR (CHCl3): 3437, 3033, 3022, 3014, 2925, 2870, 1739, 1708, 1655, 1595, 1520, 1472/cm.
[α]D = +55,0° (MeOH, c = 1,00, 22°C).
Nr. 2a-92
[α]D = +50,3° (MeOH, c = 1,00, 22°C).
Nr. 2a-93
CDCl3 300 MHz
0,95 (1H, d, J = 10,5 Hz), 1,12 und 1,23 (jeweils 3H, jeweils s), 1,52–2,46 (14H, m), 4,25 (1H, m), 5,34–5,52 (2H, m), 6,12 (1H, d, 8,7 Hz), 7,07 (1H, dd, J = 3,9 und 5,1 Hz), 7,45–7,48 (2H, m).
IR (CHCl3): 3450, 3023, 3011, 2925, 2870, 1739, 1708, 1645, 1531, 1501, 1471/cm.
[α]D = +49,1° (MeOH, c = 1,02, 24°C).
Nr. 2a-94
[α]D = +51,5° (MeOH, c = 1,00, 24°C).
Nr. 2a-95
CDCl3 300 MHz
0,96 (1H, d, J = 10,5 Hz), 1,11 und 1,23 (jeweils 3H, jeweils s), 1,52–2,46 (14H, m), 4,25 (1H, m), 5,34–5,56 (2H, m), 6,14 (1H, d, 8,7 Hz), 7,34 (2H, d, J = 2,0 Hz), 7,85 (1H, t, J = 2,0 Hz).
IR (CHCl3): 3452, 3114, 3030, 3013, 2925, 2870, 1708, 1649, 1535, 1498, 1471/cm.
[α]D = +55,5° (MeOH, c = 1,00, 25°C).
Schmp. 87,0–88,0°C.
Nr. 2a-96
CD3OD 300 MHz
0,94 (1H, d, J = 10,2 Hz), 1,13 und 1,22 (jeweils 3H, jeweils s), 1,50–1,76 (3H, m), 1,94–2,39 (11H, m), 4,11 (1H, m), 5,39–5,49 (2H, m), 7,43–7,51 (2H, m), 8,05 (1H, m).
IR (KBr): 3369, 3084, 2985, 2921, 2868, 1630, 1566, 1538, 1503/cm.
[α]D = +38,8° (MeOH, c = 1,01, 22°C).
Nr. 2a-97
CD3OD 300 MHz
0,93 (1H, d, J = 9,9 Hz), 1,13 und 1,22 (jeweils 3H, jeweils s), 1,48–1,58 (3H, m), 1,96–2,36 (11H, m), 4,10 (1H, m), 5,35–5,50 (2H, m), 7,42–7,51 (2H, m), 8,06 (1H, m).
IR (KBr): 3447, 3087, 2987, 2922, 2868, 1629, 1545, 1501/cm.
[α]D = +52,9° (MeOH, c = 1,01, 24°C).
Nr. 2a-98
[α]D = +53,2° (MeOH, c = 1,02, 23°C).
Nr. 2a-99
CDCl3 300 MHz
0,97 (1H, d, J = 10,2 Hz), 1,12 und 1,22 (jeweils 3H, jeweils s), 1,26–2,45 (24H, m), 4,25 (2H, m), 5,34–5,52 (2H, m), 6,18 (1H, d, 8,7 Hz), 6,91 und 7,66 (jeweils 2H, jeweils d, J = 9,0 Hz).
IR (CHCl3): 3455, 3029, 3019, 2939, 2862, 1738, 1709, 1645, 1605, 1523, 1494/cm.
[α]D = +51,4° (MeOH, c = 1,00, 23°C).
Nr. 2a-100
[α]D = +49,3° (MeOH, c = 1,00, 24°C).
Nr. 2a-101
[α]D = +51,3° (MeOH, c = 1,00, 24°C).
Nr. 2a-102
[α]D = +48,8° (MeOH, c = 1,01, 23°C).
Nr. 2a-103
CDCl3 300 MHz
0,94 (1H, d, J = 10,2 Hz), 1,12 und 1,22 (jeweils 3H, jeweils s), 1,52–2,46 (14H, m), 2,48 (3H, d, J = 0,3 Hz), 4,20 (1H, m), 5,32–5,54 (2H, m), 6,46 (1H, br), 7,12 (1H, d, J = 9,0 Hz).
IR (CHCl3): 3415, 3144, 3029, 3011, 2926, 2871, 1708, 1671, 1598, 1538, 14564/cm
[α]D = +49,6° (MeOH, c = 1,01, 23°C).
Nr. 2a-104
[α]D = +77,0° (MeOH, c = 1,02, 23°C).
Nr. 2a-105
CDCl3 300 MHz
93 (1H, d, J = 9,9 Hz), 1,09 und 1,21 (jeweils 3H, jeweils s), 1,51–2,44 (14H, m), 3,90 (6H, s), 4,20 (1H, m), 5,38–5,50 (2H, m), 5,87 (1H, d, J = 9,0 Hz), 6,25 und 7,54 (jeweils 1H, jeweils d, J = 15,6 Hz), 6,84 (1H, d, J = 8,1 Hz), 7,03 (1H, d, J = 1,8 Hz), 7,09 (1H, dd, J = 1,8 und 8,1 Hz).
IR (CHCl3): 3439, 3028, 3012, 2937, 2871, 2841, 1739, 1708, 1661, 1620, 1600, 1513/cm.
[α]D = +77,3° (MeOH, c = 1,01, 23°C).
Nr. 2a-106
[α]D = +67,0° (MeOH, c = 1,00, 25°C).
Nr. 2a-107
[α]D = +66,6° (MeOH, c = 1,01, 24°C).
Schmp. 168,0–170,0°C.
Nr. 2a-108
[α]D = +61,8° (MeOH, c = 1,00, 22°C).
Nr. 2a-109
CDCl3 300 MHz
0,96 (1H, d, J = 10,2 Hz), 1,10 und 1,22 (jeweils 3H, jeweils s), 1,51–2,45 (14H, m), 4,25 (1H, m), 5,33–5,49 (2H, m), 6,21 (1H, d, 8,7 Hz), 7,25 und 7,60 (jeweils 2H, jeweils d, 8,7 Hz), 7,33–7,41 (5H, s).
IR (CHCl3): 3453, 3062, 3028, 3014, 2925, 2870, 1739, 1708, 1651, 1594, 1557, 1515, 1481/cm.
[α]D = +61,0° (MeOH, c = 1,01, 22°C).
Nr. 2a-110
CD3OD 300 MHz
0,94 (1H, d, J = 9,9 Hz), 1,13 und 1,22 (jeweils 3H, jeweils s), 1,54–2,37 (14H, m), 4,12 (1H, m), 5,38–5,49 (2H, m), 7,25 und 7,68 (jeweils 2H, jeweils d, 8,7 Hz), 7,41 (5H, s).
IR (KBr): 3435, 3058, 2986, 2920, 2866, 1635, 1595, 1562, 1521, 1482, 1439, 1411/cm.
[α]D = +47,3° (MeOH, c = 1,01, 23°C).
Nr. 2a-111
[α]D = +65,6° (MeOH, c = 1,01, 24°C).
Nr. 2a-112
CDCl3 300 MHz
0,97 (1H, d, J = 10,2 Hz), 1,12 und 1,23 (jeweils 3H, jeweils s), 1,51–2,46 (14H, m), 4,27 (1H, m), 5,35–5,50 (2H, m), 6,22 (1H, d, J = 8,4 Hz), 7,40 und 7,66 (jeweils 2H, jeweils d, J = 9,0 Hz).
IR (CHCl3): 3439, 3028, 3012, 2937, 2871, 2841, 1739, 1708, 1661, 1620, 1600, 1513/cm.
[α]D = +65,6° (MeOH, c = 1,01, 22°C).
Nr. 2a-113
[α]D = +59,6° (MeOH, c = 1,00, 24°C).
Nr. 2a-114
CDCl3 300 MHz
0,98 (1H, d, J = 10,2 Hz), 1,12 und 1,24 (jeweils 3H, jeweils s), 1,52–2,46 (14H, m), 4,29 (1H, m), 5,35–5,51 (2H, m), 6,28 (1H, d, J = 8,4 Hz), 7,70 und 7,83 (jeweils 2H, jeweils d, J = 8,4 Hz).
IR (CHCl3): 3439, 3028, 3012, 2937, 2871, 2841, 1739, 1708, 1661, 1620, 1600, 1513/cm.
[α]D = +60,6° (MeOH, c = 1,01, 22°C).
Nr. 2a-115
[α]D = +59,7° (MeOH, c = 0,99, 24°C).
Nr. 2a-116
CDCl3 300 MHz
0,97 (1H, d, J = 10,2 Hz), 1,12 und 1,23 (jeweils 3H, jeweils s), 1,52–2,46 (14H, m), 2,39 (3H, s), 4,27 (1H, m), 5,33–5,51 (2H, m), 6,24 (1H, d, J = 9,0 Hz), 7,23 und 7,62 (jeweils 2H, jeweils d, J = 8,4 Hz).
IR (CHCl3): 3439, 3028, 3012, 2937, 2871, 2841, 1739, 1708, 1661, 1620, 1600, 1513/cm.
[α]D = +59,7° (MeOH, c = 0,99, 24°C).
Nr. 2a-117
[α]D = +56,7° (MeOH, c = 1,00, 23°C).
Nr. 2a-118
CDCl3 300 MHz
0,96 (1H, d, J = 10,2 Hz), 1,11 und 1,23 (jeweils 3H, jeweils s), 1,53–2,44 (14H, m), 4,23 (1H, m), 5,34–5,51 (2H, m), 6,02 (2H, s), 6,13 (1H, d, J = 8,7 Hz), 6,83 (1H, dd, J = 1,2 und 7,8 Hz), 7,22–7,25 (2H, m).
IR (CHCl3): 3453, 3031, 3020, 3012, 2924, 2870, 1740, 1708, 1650, 1619, 1605, 1519, 1504, 1480/cm.
[α]D = +57,2° (MeOH, c = 1,02, 23°C).
Nr. 2a-119
CDCl3 300 MHz
0,96 (1H, d, J = 10,5 Hz), 1,07 und 1,23 (jeweils 3H, jeweils s), 1,51–2,44 (14H, m), 2,32 (3H, s), 4,26 (1H, m), 5,37–5,52 (2H, m), 6,40 (1H, d, J = 9,0 Hz), 7,09 (1H, m), 7,30 (1H, m), 7,46 (1H, m), 7,66 (1H, m).
IR (CHCl3): 3443, 3028, 3012, 2925, 2870, 1766, 1747, 1709, 1657, 1607, 1516, 1479/cm.
[α]D = +53,2° (MeOH, c = 0,99, 21°C).
Nr. 2a-120
CDCl3 300 MHz
0,98 (1H, d, J = 10,2 Hz), 1,14 und 1,24 (jeweils 3H, jeweils s), 1,53–2,44 (14H, m), 4,30 (1H, m), 5,35–5,52 (2H, m), 6,42 (1H, d, 8,7 Hz), 6,85 (1H, m), 6,99 (1H, dd, J = 1,2 und 8,4 Hz), 7,27 (1H, m), 7,39 (1H, m).
IR (CHCl3): 3463, 3033, 3021, 3014, 2992, 2924, 2870, 1708, 1643, 1597, 1523, 1488/cm.
[α]D = +46,3° (MeOH, c = 1,01, 21°C).
Nr. 2a-121
CDCl3 300 MHz
0,98 (1H, d, J = 10,2 Hz), 1,14 und 1,23 (jeweils 3H, jeweils s), 1,47–2,47 (14H, m), 3,95 (3H, s), 4,31 (1H, m), 5,32–5,50 (2H, m), 6,98 (1H, dd, J = 0,9 und 8,4 Hz), 7,09 (1H, ddd, J = 0,9, 7,7 und 8,4 Hz), 7,45 (1H, m), 8,19 (1H, dd, J = 2,1 und 8,1 Hz), 8,32 (1H, d, J = 9,0 Hz).
IR (CHCl3): 3400, 3078, 3028, 3020, 3007, 2924, 2870, 2842, 1736, 1708, 1640, 1600, 1536, 1483, 1470/cm.
[α]D = +38,1° (MeOH, c = 1,02, 23°C).
Nr. 2a-122
[α]D = +42,3° (MeOH, c = 0,99, 23°C).
Nr. 2a-123
[α]D = +38,7° (MeOH, c = 1,00, 21°C).
Nr. 2a-124
[α]D = +45,0° (MeOH, c = 1,01, 21°C).
Schmp. 119,0–120,0°C.
Nr. 2a-125
[α]D = +49,8° (MeOH, c = 1,01, 22°C).
Nr. 2a-126
CDCl3 300 MHz
0,97 (1H, d, J = 10,2 Hz), 1,11 und 1,23 (jeweils 3H, jeweils s), 1,52–2,47 (14H, m), 4,26 (1H, m), 5,34–5,50 (2H, m), 6,22 (1H, d, 8,7 Hz), 7,55–7,61 (4H, m).
IR (CHCl3): 3400, 3078, 3028, 3020, 3007, 2924, 2870, 2842, 1736, 1708, 1640, 1600, 1536, 1483, 1470/cm.
[α]D = +63,0° (MeOH, c = 1,01, 23°C).
Nr. 2a-127
CDCl3 300 MHz
0,91 (1H, d, J = 10,2 Hz), 1,10 und 1,20 (jeweils 3H, jeweils s), 1,50–2,42 (14H, m), 4,23 (1H, m), 5,31–5,51 (2H, m), 6,45 (1H, d, J = 8,4 Hz), 7,01 (1H, t, J = 7,4 Hz), 7,22–7,27 (2H, m), 7,33–7,40 (4H, m), 7,53 (2H, d, J = 9,0, Hz), 8,30 und 8,48 (jeweils 1H, jeweils s).
IR (CHCl3): 3452, 3028, 3022, 3015, 2925, 2870, 1708, 1654, 1590, 1514, 1478/cm.
[α]D = +59,5° (MeOH, c = 1,01, 23°C).
Nr. 2a-128
d6-DMSO 300 MHz
0,84 (1H, d, J = 9,9 Hz), 1,06 und 1,19 (jeweils 3H, jeweils s), 1,37–2,37 (14H, m), 3,79 (1H, m), 5,35–5,51 (2H, m), 6,08 (1H, d, 8,7 Hz), 6,85–6,90 (1H, m), 7,18–7,23 (2H, m), 7,35–7,38 (2H, m), 8,42 (1H, s), 12,00 (1H, s).
IR (Nujol): 3395, 3345, 2925, 2866, 2623, 2506, 1697, 1658, 1638, 1597, 1557/cm.
[α]D = +26,0° (MeOH, c = 1,01, 23°C).
Schmp. 164,0–166,0°C.
Nr. 2a-129
CDCl3 300 MHz
1,01 (1H, d, J = 10,0 Hz), 1,17 und 1,25 (jeweils 3H, jeweils s), 1,54–2,52 (14H, m), 4,34 (1H, m), 5,36–5,57 (2H, m), 6,42 (1H, d, J = 8,6 Hz), 7,51–7,60 (2H, m), 7,77 (1H, dd, J = 1,8 und 8,6 Hz), 7,85–7,96 (3H, m), 8,24 (1H, br).
IR (CHCl3): 3451, 3060, 3028, 3010, 2925, 2870, 1708, 1652, 1629, 1600, 1517, 1502/cm.
[α]D = +68,6° (MeOH, c = 1,00, 22°C).
Nr. 2a-130
CDCl3 300 MHz
1,02 (1H, d, J = 10,2 Hz), 1,04 und 1,26 (jeweils 3H, jeweils s), 1,54–2,52 (14H, m), 4,41 (1H, m), 5,41–5,58 (2H, m), 6,14 (1H, d, J = 9,0 Hz), 7,43–7,59 (4H, m), 7,85–7,92 (2H, m), 8,27 (1H, dd, J = 1,8 und 7,2 Hz).
IR (CHCl3): 3436, 3032, 3010, 2924, 2870, 2664, 1708, 1652, 1512, 1498/cm.
[α]D = +93,9° (MeOH, c = 1,00, 22°C).
Schmp. 94,0–96,0°C.
Nr. 2a-131
[α]D = +50,2° (MeOH, c = 0,95, 21°C).
Nr. 2a-132
[α]D = +10,9° (MeOH, c = 0,92, 21°C).
Nr. 2a-133
[α]D = +60,4° (MeOH, c = 1,00, 21°C).
Nr. 2a-134
[α]D = +38,5° (MeOH, c = 1,01, 23°C).
Nr. 2a-135
[α]D = +52,5° (MeOH, c = 1,01, 23°C).
Schmp. 180,0–182,0°C.
Nr. 2a-136
[α]D = +35,3° (MeOH, c = 1,02, 23°C).
Schmp. 79,0–80,0°C.
Nr. 2a-137
CDCl3 300 MHz
0,97 (1H, d, J = 10,2 Hz), 1,11 und 1,22 (jeweils 3H, jeweils s), 1,43 (3H, t, J = 6,9 Hz), 1,52–2,44 (14H, m), 4,03 (2H, q, J = 6,9 Hz), 4,26 (1H, m), 5,33–5,50 (2H, m), 6,19 (1H, d, 8,7 Hz), 6,88–7,00 (6H, m), 7,65–7,68 (2H, m).
IR (CHCl3): 3455, 3031, 3024, 3014, 2988, 2925, 2870, 1741, 1708, 1649, 1602, 1521, 1504, 1490/cm.
[α]D = +52,0° (MeOH, c = 1,01, 23°C).
Nr. 2a-138
CDCl3 300 MHz
0,97 (1H, d, J = 10,2 Hz), 1,11 und 1,22 (jeweils 3H, jeweils s), 1,35 (6H, d, J = 6,0 Hz), 1,53–2,46 (14H, m), 4,25 (1H, m), 4,51 (1H, m), 5,33–5,50 (2H, m), 6,12 (1H, d, J = 9,0 Hz), 6,87–6,99 (6H, m), 7,65–7,68 (2H, m).
IR (CHCl3): 3454, 3031, 3014, 2980, 2925, 2870, 1741, 1708, 1649, 1602, 1522, 1490/cm.
[α]D = +50,0° (MeOH, c = 1,05, 22°C).
Nr. 2a-139
CDCl3 300 MHz
1,00 (1H, d, J = 10,2 Hz), 1,16 und 1,24 (jeweils 3H, jeweils s), 1,59–2,52 (14H, m), 4,31 (1H, m), 5,40–5,53 (2H, m), 6,36 (1H, d, 8,7 Hz), 6,70 (1H, d, J = 1,5 Hz), 7,12 (1H, m), 7,30 (1H, m), 7,47 (1H, dd, J = 0,6 und 8,1 Hz), 7,61 (1H, d, J = 8,4 Hz).
IR (CHCl3): 3449, 3243, 3029, 3022, 3013, 2925, 2871, 1707, 1631, 1542, 1505/cm.
[α]D = +63,4° (MeOH, c = 1,00, 23°C).
Schmp. 178,0–179,0°C.
Nr. 2a-140
CDCl3 300 MHz
0,97 (1H, d, J = 10,2 Hz), 1,18 und 1,23 (jeweils 3H, jeweils s), 1,57–2,50 (14H, m), 4,35 (1H, m), 5,32–5,55 (2H, m), 6,42 (1H, d, 8,7 Hz), 6,70 (1H, d, J = 1,5 Hz), 7,21–7,24 (2H, m), 7,46 (1H, m), 7,76 (1H, m), 7,86 (1H, d, J = 3,0 Hz), 10,20 (1H, s).
IR (CHCl3): 3465, 3010, 2924, 1739, 1604, 1546, 1504/cm.
[α]D = +39,4° (MeOH, c = 1,01, 22°C).
Schmp. 167,0–168,0°C.
Nr. 2a-141
CDCl3 300 MHz
0,99 (1H, d, J = 10,2 Hz), 1,14 und 1,24 (jeweils 3H, jeweils s), 1,55–2,44 (14H, m), 3,84 (3H, s), 4,27 (1H, m), 5,34–5,52 (2H, m), 6,28 (1H, d, J = 9,0 Hz), 6,91 und 7,47 (jeweils 2H, jeweils d, J = 9,0 Hz), 6,98 und 7,14 (jeweils 1H, jeweils d, J = 16,5 Hz), 7,54 und 7,70 (jeweils 2H, jeweils d, 8,7 Hz).
IR (CHCl3): 3453, 3025, 3015, 2925, 2870, 2839, 1740, 1708, 1649, 1602, 1510, 1493, 1470/cm.
[α]D = +73,4° (MeOH, c = 1,02, 22°C).
Schmp. 155,0–157,0°C.
Nr. 2a-142
CDCl3 300 MHz
0,97 (1H, d, J = 10,2 Hz), 1,11 und 1,23 (jeweils 3H, jeweils s), 1,52–2,45 (14H, m), 3,79 (3H, s), 4,27 (1H, m), 5,34–5,50 (2H, m), 6,24 (1H, d, J = 9,0 Hz), 6,49 und 6,62 (jeweils 1H, jeweils d, J = 12,3 Hz), 6,77 und 7,16 (jeweils 2H, jeweils d, 8,7 Hz), 7,32 und 7,59 (jeweils 2H, jeweils d, J = 8,1 Hz).
IR (CHCl3): 3453, 3025, 3014, 2925, 2870, 2839, 1739, 1708, 1649, 1606, 1510, 1494/cm.
[α]D = +60,7° (MeOH, c = 0,99, 22°C).
Nr. 2a-143
[α]D = +57,3° (MeOH, c = 1,01, 23°C).
Nr. 2a-144
[α]D = +12,2° (MeOH, c = 1,00, 23°C).
Schmp. 114,0–116,0°C.
Nr. 2a-145
CDCl3 300 MHz
0,95 (1H, d, J = 10,2 Hz), 1,10 und 1,21 (jeweils 3H, jeweils s), 1,52–2,44 (14H, m), 4,25 (1H, m), 5,33–5,49 (2H, m), 6,37 (1H, d, 8,7 Hz), 7,45–7,47 (3H, m), 7,62–7,66 (2H, m), 7,69 und 7,80 (jeweils 2H, jeweils d, J = 7,5 Hz).
IR (CHCl3): 3449, 3058, 3027, 3012, 2925, 2870, 1708, 1655, 1513, 1481, 1043/cm.
[α]D = +61,0° (MeOH, c = 1,01, 23°C).
Nr. 2a-146
CDCl3 300 MHz
0,95 (1H, d, J = 10,5 Hz), 1,09 und 1,21 (jeweils 3H, jeweils s), 1,50–2,41 (14H, m), 4,25 (1H, m), 5,33–5,49 (2H, m), 6,33 (1H, d, J = 8,4 Hz), 7,49–7,61 (3H, m), 7,91–7,92 (2H, m), 7,82 und 7,97 (jeweils 2H, jeweils d, 8,7 Hz).
IR (CHCl3): 3447, 3029, 3023, 3015, 2925, 2870, 1708, 1660, 1514, 1484, 1321, 1161/cm.
[α]D = +62,0° (MeOH, c = 1,00, 22°C).
Nr. 2a-147
CDCl3 300 MHz
0,97 (1H, d, J = 10,2 Hz), 1,12 und 1,23 (jeweils 3H, jeweils s), 1,52–2,46 (14H, m), 2,51 (3H, s), 4,26 (1H, m), 5,34–5,51 (2H, m), 6,23 (1H, d, J = 8,4 Hz), 7,26 und 7,64 (jeweils 2H, jeweils d, J = 8,4 Hz).
IR (CHCl3): 3453, 3027, 3015, 2925, 2870, 2665, 1708, 1648, 1596, 1516, 1484/cm.
[α]D = +67,7° (MeOH, c = 0,82, 22°C).
Nr. 2a-148
[α]D = +72,5° (MeOH, c = 1,01, 25°C).
Nr. 2a-149
[α]D = +67,8° (MeOH, c = 0,98, 25°C).
Nr. 2a-150
CDCl3 300 MHz
0,94 (1H, d, J = 10,2 Hz), 1,10 und 1,23 (jeweils 3H, jeweils s), 1,52–2,50 (14H, m), 4,22 (1H, m), 5,36–5,55 (2H, m), 6,48 (1H, d, J = 8,4 Hz), 8,35 (1H, s), 8,90 (1H, s).
IR (CHCl3): 3443, 3374, 3091, 3024, 3012, 2925, 2871, 1709, 1652, 1525, 1494/cm.
[α]D = +58,1° (MeOH, c = 1,01, 23°C).
Schmp. 120,0–122,0°C.
Nr. 2a-151
[α]D = +40,6° (MeOH, c = 1,01, 23°C).
Nr. 2a-152
CDCl3 300 MHz
0,96 (1H, d, J = 10,5 Hz), 1,10 und 1,24 (jeweils 3H, jeweils s), 1,50–2,50 (14H, m), 2,71 (3H, s), 4,26 (1H, m), 5,37–5,51 (2H, m), 6,02 (1H, d, J = 9,0 Hz), 8,73 (1H, s).
IR (CHCl3): 3463, 3435, 3087, 3025, 3014, 2925, 2870, 1708, 1649, 1523, 1503/cm.
[α]D = +54,1° (MeOH, c = 1,02, 22°C).
Nr. 2a-153
CDCl3 300 MHz
0,95 (1H, d, J = 9,9 Hz), 1,11 und 1,23 (jeweils 3H, jeweils s), 1,50–2,50 (14H, m), 2,50 (3H, s), 4,26 (1H, m), 5,36–5,51 (2H, m), 6,01 (1H, d, J = 8,4 Hz), 6,88 (1H, d, J = 5,1 Hz), 7,26 (1H, d, J = 5,1 Hz).
IR (CHCl3): 3469, 3431, 3025, 3013, 2925, 2871, 2664, 1708, 1639, 1544, 1505/cm.
[α]D = +35,8° (MeOH, c = 1,03, 22°C).
Nr. 2a-154
CDCl3 300 MHz
0,95 (1H, d, J = 9,9 Hz), 1,10 und 1,22 (jeweils 3H, jeweils s), 1,52–2,46 (14H, m), 2,51 (3H, d, J = 1,2 Hz), 4,26 (1H, m), 5,34–5,50 (2H, m), 6,00 (1H, d, J = 8,4 Hz), 6,73 (1H, dd, J = 5,1 und 3,6 Hz), 7,29 (1H, d, J = 3,6 Hz).
IR (CHCl3): 3450, 3431, 3026, 3011, 2925, 2869, 1739, 1708, 1639, 1547, 1508/cm.
[α]D = +50,5° (MeOH, c = 1,01, 22°C).
Nr. 2a-155
CDCl3 300 MHz
0,99 (1H, d, J = 10,2 Hz), 1,19 und 1,25 (jeweils 3H, jeweils s), 1,53–2,48 (14H, m), 4,31 (1H, m), 5,36–5,51 (2H, m), 6,79 (1H, d, J = 9,3 Hz), 7,29 (1H, m), 7,41 (1H, m), 7,48 (1H, s), 7,51 (1H, m), 7,66 (1H, d, J = 8,1 Hz).
IR (CHCl3): 3436, 3029, 3024, 3015, 2925, 2871, 2670, 1708, 1659, 1598, 1510/cm.
[α]D = +69,1° (MeOH, c = 1,01, 22°C).
Nr. 2a-156
CDCl3:CD3OD = 10:1, 300 MHz
0,99 (1H, d, J = 9,9 Hz), 1,11 und 1,21 (jeweils 3H, jeweils s), 1,56–2,58 (14H, m), 4,22 (1H, m), 5,35–5,59 (2H, m), 6,83 (1H, d, J = 8,4 Hz), 7,48 (1H, d, J = 8,4 Hz), 7,61 (1H, dd, J = 1,5 und 8,4 Hz), 8,09 (1H, d, J = 1,5 Hz), 8,12 (1H, s).
IR (KBr): 3422, 3115, 2985, 2922, 2869, 2609, 1708, 1636, 1578, 1529, 1470/cm.
[α]D = +62,8° (MeOH, c = 1,01, 22°C).
Nr. 2a-157
[α]D = +40,0° (MeOH, c = 0,95, 22°C).
Nr. 2a-158
CDCl3 300 MHz
1,00 (1H, d, J = 10,5 Hz), 1,17 und 1,24 (jeweils 3H, jeweils s), 1,54–2,50 (14H, m), 4,34 (1H, m), 5,36–5,52 (2H, m), 7,80 (1H, d, J = 9,0 Hz), 9,30 (1H, s).
IR (CHCl3): 3410, 3122, 3030, 3012, 2925, 2871, 2668, 1709, 1667, 1538, 1466/cm.
[α]D = +44,9° (MeOH, c = 0,99, 22°C).
Nr. 2a-159
CDCl3 300 MHz
0,97 (1H, d, J = 10,2 Hz), 1,13 und 1,22 (jeweils 3H, jeweils s), 1,55–2,43 (14H, m), 3,03 (6H, s), 4,23 (1H, m), 5,32–5,51 (2H, m), 6,16 (1H, d, 8,7 Hz), 6,87 und 7,63 (jeweils 2H, jeweils d, 8,7 Hz).
IR (CHCl3): 3457, 3028, 3006, 2924, 2870, 2654, 1739, 1709, 1637, 1608, 1608, 1534, 1501/cm.
[α]D = +64,8° (MeOH, c = 1,01, 22°C).
Nr. 2a-160
d6-DMSO 300 MHz
0,83 (1H, d, J = 9,9 Hz), 1,02 und 1,19 (jeweils 3H, jeweils s), 1,38–1,61 (3H, m), 1,90–2,32 (11H, m), 3,90 (1H, m), 5,41–5,44 (2H, m), 7,32 (1H, dd, J = 0,9 und 7,2 Hz), 7,45–7,60 (2H, m), 7,77 (1H, dd, J = 0,9 und 7,8 Hz), 8,03 (1H, d, J = 6,9 Hz), 12,40 (1H, s).
IR (Nujol): 3315, 2924, 2856, 2656, 2535, 1737, 1703, 1637, 1598, 1581, 1541/cm.
[α]D = +78,5° (MeOH, c = 1,01, 24°C).
Schmp. 161,0–162,0°C.
Nr. 2a-161
[α]D = +65,3° (MeOH, c = 1,00, 22°C).
Nr. 2a-162
CDCl3 300 MHz
0,99 (1H, d, J = 10,2 Hz), 1,13 und 1,25 (jeweils 3H, jeweils s), 1,53–2,45 (14H, m), 4,30 (1H, m), 5,36–5,51 (2H, m), 6,32 (1H, d, J = 8,4 Hz), 7,88 und 8,28 (jeweils 2H, jeweils d, J = 9,0 Hz).
IR (CHCl3): 3448, 3029, 3016, 2925, 2870, 1708, 1664, 1602, 1527, 1484, 1347/cm.
[α]D = +72,7° (MeOH, c = 1,02, 22°C).
Nr. 2a-163
CDCl3 300 MHz.
0,96 (1H, d, J = 10,2 Hz), 1,11 und 1,23 (jeweils 3H, jeweils s), 1,55–2,51 (14H, m), 4,26 (1H, m), 5,36–5,57 (2H, m), 6,68 (1H, d, J = 7,8 Hz), 7,41 (1H, dd, J = 4,8 und 8,1 Hz), 8,20 (1H, d, J = 8,1 Hz), 8,66 (1H, d, J = 4,8 Hz), 9,00 (1H, s).
IR (CHCl3): 3448, 3026, 3013, 2925, 2870, 2534, 1709, 1658, 1590, 1515, 1471/cm.
[α]D = +71,3° (MeOH, c = 1,01, 22°C).
Nr. 2a-164
[α]D = +40,8° (MeOH, c = 0,98, 22°C).
Nr. 2a-165
CDCl3 300 MHz
0,96 (1H, d, J = 10,5 Hz), 1,11 und 1,24 (jeweils 3H, jeweils s), 1,55–2,52 (14H, m), 4,24 (1H, m), 5,37–5,57 (2H, m), 6,63 (1H, d, J = 7,8 Hz), 7,59 und 8,63 (jeweils 2H, jeweils d, J = 6,0 Hz).
IR (CHCl3): 3447, 3346, 3028, 3016, 2925, 2870, 2538, 1941, 1708, 1662, 1556, 1516/cm.
[α]D = +75,4° (MeOH, c = 1,01, 22°c).
Nr. 2a-166
CDCl3 300 MHz
0,97 (1H, d, J = 10,2 Hz), 1,11 und 1,22 (jeweils 3H, jeweils s), 1,51–2,44 (14H, m), 2,95 (6H, s), 4,25 (1H, m), 5,33–5,50 (2H, m), 6,19 (1H, d, 8,7 Hz), 6,77 und 6,97 (jeweils 2H, jeweils d, J = 8,4 Hz), 6,94 und 7,65 (jeweils 2H, jeweils d, J = 9,0 Hz).
IR (CHCl3): 3453, 3024, 3016, 2924, 2871, 2806, 1739, 1708, 1647, 1612, 1604, 1515, 1490/cm.
[α]D = +53,1° (MeOH, c = 1,02, 23°C).
Schmp. 104,0–105,5°C.
Nr. 2a-167
CDCl3 300 MHz
1,01 (1H, d, J = 9,9 Hz), 1,19 und 1,26 (jeweils 3H, jeweils s), 1,56–2,53 (14H, m), 4,37 (1H, m), 5,35–5,55 (2H, m), 6,47 (1H, d, J = 8,4 Hz), 7,61–7,71 (2H, m), 7,79 (2H, s), 7,89–7,97 (2H, m), 8,27 (1H, d, J = 2, 1 Hz), 8,66–8,73 (2H, m).
IR (CHCl3): 3450, 3024, 3014, 2925, 2870, 2667, 1707, 1650, 1531, 1509/cm.
[α]D = +70,5° (MeOH, c = 1,00, 22°C).
Nr. 2a-168
CDCl3 300 MHz
1,02 (1H, d, J = 10,2 Hz), 1,20 und 1,26 (jeweils 3H, jeweils s), 1,56–2,50 (14H, m), 4,38 (1H, m), 5,36–5,56 (2H, m), 6,51 (1H, d, J = 8,4 Hz), 7,61–7,93 (7H, m), 8,74 (1H, d, J = 8,4 Hz), 9,15 (1H, s).
IR (CHCl3): 3517, 3451, 3060, 3028, 3011, 2925, 2870, 2664, 1709, 1651, 1519, 1498/cm.
[α]D = +54,4° (MeOH, c = 1,00, 23°C).
Nr. 2a-169
CDCl3 300 MHz
0,96 (1H, d, J = 10,5 Hz), 1,09 und 1,21 (jeweils 3H, jeweils s), 1,50–2,44 (14H, m), 3,85 (3H, s), 4,24 (1H, m), 5,32–5,48 (2H, m), 6,19 (1H, d, J = 8,4 Hz), 6,94 und 7,45 (jeweils 2H, jeweils d, J = 9,0 Hz), 7,11 und 7,45 (jeweils 2H, jeweils d, 8,7 Hz).
IR (CHCl3): 3516, 3453, 3029, 3009, 2925, 2870, 2840, 2665, 1708, 1650, 1593, 1515, 1493, 1482/cm.
[α]D = +57,8° (MeOH, c = 1,00, 23°C).
Nr. 2a-170
CDCl3 300 MHz
0,98 (1H, d, J = 10,2 Hz), 1,15 und 1,24 (jeweils 3H, jeweils s), 1,52–2,50 (14H, m), 4,28 (1H, m), 5,33–5,54 (2H, m), 6,25 (1H, d, J = 8,2 Hz), 7,38–7,44 (2H, m), 7,74 (1H, s), 7,81–7,86 (2H, m).
IR (CHCl3): 3517, 3448, 3427, 3024, 3013, 2925, 2870, 2669, 1708, 1650, 1562, 1535, 1500/cm.
[α]D = +61,6° (MeOH, c = 1,00, 23°C).
Nr. 2a-171
CDCl3 300 MHz
0,96 (1H, d, J = 10,2 Hz, 1,11 und 1,22 (jeweils 3H, jeweils s), 1,52–2,42 (14H, m), 2,48 (3H, s), 4,21 (1H, m), 5,31–5,52 (2H, m), 6,06 (1H, d, J = 8,2 Hz), 6,97 und 7,59 (jeweils 1H, jeweils d, J = 1,2 Hz).
IR (CHCl3): 3452, 3113, 3028, 3007, 2925, 2870, 2669, 1708, 1645, 1554, 1509/cm.
[α]D = +52,4° (MeOH, c = 1,00, 23°C).
Nr. 2a-172
CDCl3 300 MHz
0,96 (1H, d, J = 10,2 Hz), 1,09 und 1,28 (jeweils 3H, jeweils s), 1,50–2,40 (14H, m), 2,69 (3H, s), 4,24 (1H, m), 5,35–5,51 (2H, m), 5,96 (1H, d, 8,7 Hz), 7,03 und 7,07 (jeweils 1H, jeweils d, J = 5,4 Hz).
IR (CHCl3): 3451, 3031, 3013, 2925, 2870, 2666, 1708, 1647, 1542, 1497/cm.
[α]D = +51,2° (MeOH, c = 1,00, 23°C).
Nr. 2a-173
CDCl3 300 MHz
0,95 (1H, d, J = 10,2 Hz), 1,10 und 1,23 (jeweils 3H, jeweils s), 1,50–2,45 (14H, m), 4,22 (1H, m), 5,35–5,49 (2H, m), 6,05 (1H, d, J = 8,4 Hz), 7,26
und 7,75 (jeweils 1H, jeweils d, J = 1,5 Hz).
IR (CHCl3): 3451, 3011, 3029, 3011, 2925, 2870, 1708, 1652, 1538, 1500/cm.
[α]D = +50,6° (MeOH, c = 1,01, 23°C).
Nr. 2a-174
CDCl3 300 MHz
0,96 (1H, d, J = 10,2 Hz), 1,13 und 1,23 (jeweils 3H, jeweils s), 1,52–2,50 (14H, m), 4,29 (1H, m), 5,35–5,51 (2H, m), 7,02 (1H, d, J = 8,4 Hz), 7,32 und 8,16 (jeweils 1H, jeweils d, J = 3,9 Hz).
IR (CHCl3): 3417, 3115, 3023, 3014, 2925, 2870, 1708, 1645, 1530/cm.
[α]D = +48,8° (MeOH, c = 1,02, 23°C).
Nr. 2a-175
CDCl3 300 MHz
0,97 (1H, d, J = 10,2 Hz), 1,14 und 1,23 (jeweils 3H, jeweils s), 1,50–2,52 (14H, m), 2,52 (3H, s), 4,29 (1H, m), 5,34–5,51 (2H, m), 7,78 (1H, d, J = 9,0 Hz), 7,24 und 7,52 (jeweils 1H, jeweils d, J = 5,4 Hz).
IR (CHCl3): 3329, 3093, 3023, 3015, 2924, 2871, 1708, 1640, 1526/cm.
[α]D = +45,0° (MeOH, c = 1,01, 23°C).
Nr. 2a-176
CDCl3 300 MHz
0,95 (1H, d, J = 10,5 Hz), 1,09 und 1,23 (jeweils 3H, jeweils s), 1,52–2,46 (14H, m), 2,40 (3H, d, J = 0,9 Hz), 4,24 (1H, m), 5,35–5,51 (2H, m), 6,05 (1H, d, 8,7 Hz), 6,95 (1H, m), 7,57 (1H, d, J = 3,3 Hz).
IR (CHCl3): 3517, 3444, 3103, 3024, 3013, 2926, 2870, 1739, 1748, 1649, 1636, 1507/cm.
[α]D = +54,8° (MeOH, c = 1,01, 23°C).
Schmp. 97,0–99,0°C.
Nr. 2a-177
CDCl3 300 MHz
0,97 (1H, d, J = 10,2 Hz), 1,11 und 1,23 (jeweils 3H, jeweils s), 1,52–2,45 (14H, m), 3,93 (3H, s), 4,27 (1H, m), 5,34–5,50 (2H, m), 6,35 (1H, d, J = 3,3 Hz), 7,80 (1H, d, 8,7 Hz), 8,10 (1H, d, J = 3,3 Hz).
IR (CHCl3): 3395, 3121, 3031, 3019, 3012, 2925, 2871, 1739, 1709, 1640, 1557, 1533/cm.
[α]D = +22,8° (MeOH, c = 1,01, 23°C).
Schmp. 109,0–112,0°C.
Nr. 2a-178
CDCl3 300 MHz
0,96 (1H, d, J = 10,5 Hz), 1,10 und 1,23 (jeweils 3H, jeweils s), 1,51–2,45 (14H, m), 4,24 (1H, m), 5,35–5,50 (2H, m), 6,09 (1H, d, J = 8,4 Hz), 7,17–7,31 (6H, m), 7,95 (1H, d, J = 1,5 Hz).
IR (CHCl3): 3510, 3451, 3062, 3031, 3022, 3011, 2925, 2870, 2662, 1708, 1651, 1582, 1535, 1497, 1477/cm.
[α]D = +47,9° (MeOH, c = 1,01, 25°C).
Nr. 2a-179
CDCl3 300 MHz
0,96 (1H, d, J = 10,2 Hz), 1,14 und 1,24 (jeweils 3H, jeweils s), 1,52–2,48 (14H, m), 4,30 (1H, m), 5,36–5,52 (2H, m), 6,73 (1H, d, J = 9,0 Hz), 6,26 und 7,37 (jeweils 1H, jeweils d, J = 6,0 Hz).
IR (CHCl3): 3509, 3429, 3115, 3094, 3025, 3014, 2925, 2871, 2666, 1708, 1649, 1529, 1510/cm.
[α]D = +51,0° (MeOH, c = 1,02, 25°C).
Nr. 2a-180
CDCl3 300 MHz
0,95 (1H, d, J = 10,2 Hz), 1,14 und 1,24 (jeweils 3H, jeweils s), 1,52–2,46 (14H, m), 3,89 (3H, s), 4,21 (1H, m), 5,35–5,50 (2H, m), 6,05 (1H, d, J = 8,4 Hz), 6,46 und 7,04 (jeweils 1H, jeweils d, J = 1,8 Hz).
IR (CHCl3): 3516, 3450, 3114, 3031, 3010, 2925, 2871, 1708, 1648, 1546, 1511, 1477/cm.
[α]D = +49,1° (MeOH, c = 1,01, 25°C).
Nr. 2a-181
CDCl3 300 MHz
0,97 (1H, d, J = 10,2 Hz), 1,14 und 1,23 (jeweils 3H, jeweils s), 1,52–2,48 (14H, m), 2,42 (3H, s), 4,31 (1H, m), 5,34–5,52 (2H, m), 8,07 (1H, d, J = 9,3 Hz), 7,27 und 8,17 (jeweils 1H, jeweils d, J = 3,3 Hz).
IR (CHCl3): 3510, 3301, 3112, 3023, 3007, 2924, 2871, 2663, 1708, 1636, 1534/cm.
[α]D = +41,0° (MeOH, c = 0,96, 25°C).
Nr. 2a-182
CDCl3 300 MHz
0,96 (1H, d, J = 10,2 Hz), 1,11 und 1,23 (jeweils 3H, jeweils s), 1,53–2,46 (14H, m), 2,51 (3H, s), 4,21 (1H, m), 5,35–5,51 (2H, m), 6,05 (1H, d, J = 8,1 Hz), 7,26 und 7,78 (jeweils 1H, jeweils d, J = 1,8 Hz).
IR (CHCl3): 3509, 3450, 3109, 3024, 3012, 2925, 2870, 2666, 1708, 1650, 1535, 1498, 1471/cm.
[α]D = +52,9° (MeOH, c = 0,95, 25°C).
Nr. 2a-183
CDCl3 300 MHz
0,96 (1H, d, J = 10,5 Hz), 1,12 und 1,22 (jeweils 3H, jeweils s), 1,52–2,46 (14H, m), 4,25 (1H, m), 5,33–5,51 (2H, m), 6,17 (1H, d, 8,7 Hz), 7,01–7,05 (3H, m), 7,14 und 7,62 (jeweils 2H, jeweils d, 8,7 Hz), 7,27–7,34 (2H, m).
IR (CHCl3): 3428, 3026, 3015, 2925, 2870, 2666, 1739, 1708, 1643, 1613, 1594, 1526, 1499/cm.
[α]D = +64,8° (MeOH, c = 1,02, 23°C).
Nr. 2a-184
CDCl3 300 MHz
1,01 (1H, d, J = 10,2 Hz), 1,18 und 1,26 (jeweils 3H, jeweils s), 1,55–2,50 (14H, m), 4,35 (1H, m), 5,35–5,55 (2H, m), 6,42 (1H, d, 8,7 Hz), 7,46–7,52 (2H, m), 7,73 (1H, dd, J = 1,8 und 8,4 Hz), 7,83–7,89 (2H, m), 8,21 (1H, m), 8,59 (1H, d, J = 1,5 Hz).
IR (CHCl3): 3451, 3031, 3014, 2925, 2870, 2660, 1739, 1708, 1650, 1604, 1513, 1463/cm.
[α]D = +58,3° (MeOH, c = 1,00, 23°C).
Nr. 2a-185
CDCl3 300 MHz
1,00 (1H, d, J = 10,2 Hz), 1,18 und 1,25 (jeweils 3H, jeweils s), 1,55–2,50 (14H, m), 4,34 (1H, m), 5,35–5,54 (2H, m), 6,36 (1H, d, 8,7 Hz), 7,37 (1H, t, J = 7,4 Hz), 7,50 (1H, m), 7,57–7,59 (2H, m), 7,79 (1H, dd, J = 1,8 und 8,1 Hz), 7,99 (1H, d, J = 7,8 Hz), 8,39 (1H, d, J = 1,8 Hz).
IR (CHCl3): 3451, 3030, 3020, 2870, 2665, 1708, 1652, 1632, 1603, 1586, 1514, 1469, 1448/cm.
[α]D = +59,4° (MeOH, c = 1,01, 24°C).
Nr. 2a-186
CDCl3 300 MHz
1,00 (1H, d, J = 10,5 Hz), 1,17 und 1,25 (jeweils 3H, jeweils s), 1,54–2,50 (14H, m), 4,33 (1H, m), 5,35–5,54 (2H, m), 6,37 (1H, d, 8,7 Hz), 7,37 (1H, t, J = 7,4 Hz), 7,51 (1H, t, J = 7,8 Hz), 7,56 (1H, m), 7,70 (1H, dd, J = 1,2 und 8,4 Hz), 7,97 (3H, m).
IR (CHCl3): 3451, 3030, 3014, 2924, 2870, 2671, 1739, 1708, 1652, 1577, 1517, 1488, 1471/cm.
[α]D = +72,2° (MeOH, c = 1,00, 24°C).
Nr. 2a-187
CDCl3 300 MHz
1,00 (1H, d, J = 9,8 Hz), 1,18 und 1,25 (jeweils 3H, jeweils s), 1,54–2,53 (14H, m), 4,07 (3H, s), 4,37 (1H, m), 5,30–5,54 (2H, m), 7,34 (1H, m), 7,47 (1H, s), 7,47–7,60 (2H, m), 7,93 (1H, d, J = 7,8 Hz), 8,43 (1H, s), 8,49 (1H, d, J = 9,0 Hz).
IR (CHCl3): 3397, 3074, 3027, 3020, 3009, 2924, 1738, 1708, 1647, 1633, 1534, 1465, 1453/cm.
[α]D = +43,7° (MeOH, c = 1,01, 25°C).
Nr. 2a-188
CDCl3 300 MHz
0,97 (1H, d, J = 10,2 Hz), 1,11 und 1,23 (jeweils 3H, jeweils s), 1,53–2,50 (14H, m), 4,23 (1H, m), 5,37–5,50 (2H, m), 8,10 (1H, d, J = 9,0 Hz), 6,20 (1H, m), 6,51 (1H, m), 6,97 (1H, m), 10,81 (1H, br).
IR (CHCl3): 3450, 3236, 3112, 3029, 3015, 2925, 2871, 2645, 1701, 1616, 1558, 1516/cm.
[α]D = +50,6° (MeOH, c = 1,01, 24°C).
Nr. 2a-189
CDCl3 300 MHz
0,94 (1H, d, J = 9,9 Hz), 1,11 und 1,23 (jeweils 3H, jeweils s), 1,50–2,46 (14H, m), 3,93 (3H, s), 4,18 (1H, m), 5,35–5,52 (2H, m), 6,03 (1H, d, J = 9,3 Hz), 6,09 (1H, m), 6,48 (1H, m), 6,73 (1H, m).
IR (CHCl3): 3452, 3102, 3028, 3007, 2925, 2871, 2666, 1739, 1708, 1650, 1536, 1499, 1471/cm.
[α]D = +49,8° (MeOH, c = 1,01, 23°C).
Schmp. 101,5–103,5°C.
Nr. 2a-190
CDCl3 300 MHz
0,94 (1H, d, J = 10,2 Hz), 1,11 und 1,21 (jeweils 3H, jeweils s), 1,54–2,47 (14H, m), 4,23 (1H, m), 5,33–5,52 (2H, m), 6,06 (1H, d, J = 9,0 Hz), 6,34 (1H, m), 6,75 (1H, m), 6,36 (1H, m), 9,71 (1H, br).
IR (CHCl3): 3470, 3215, 3030, 3020, 3010, 2925, 2871, 2664, 1709, 1613, 1564, 1510/cm.
[α]D = +43,3° (MeOH, c = 1,01, 24°C).
Nr. 2a-191
CDCl3 300 MHz
0,96 (1H, d, J = 10,2 Hz), 1,11 und 1,22 (jeweils 3H, jeweils s), 1,55–2,44 (14H, m), 3,66 (3H, s), 4,20 (1H, m), 5,35–5,51 (2H, m), 5,93 (1H, d, J = 8,4 Hz), 6,27 (1H, dd, J = 1,8 und 2,7 Hz), 6,56 (1H, t, J = 2,7 Hz), 7,19 (1H, t, J = 1,8 Hz).
IR (CHCl3): 3452, 3031, 3018, 3006, 2925, 2871, 2662, 1736, 1710, 1634, 1609, 1556, 1498/cm.
[α]D = +43,1° (MeOH, c = 1,01, 23°C).
Nr. 2a-192
CDCl3 300 MHz
0,96 (1H, d, J = 10,5 Hz), 1,11 und 1,21 (jeweils 3H, jeweils s), 1,43 (3H, t, J = 7,5 Hz), 1,54–2,44 (14H, m), 3,93 (2H, q, J = 7,5 Hz), 4,21 (1H, m), 5,33–5,51 (2H, m), 5,94 (1H, d, J = 8,4 Hz), 6,27 (1H, dd, J = 1,8 und 2,7 Hz), 6,62 (1H, t, J = 2,7 Hz), 7,26 (1H, t, J = 1,8 Hz).
IR (CHCl3): 3630, 3452, 3032, 3018, 3006, 2925, 2871, 2661, 1735, 1710, 1633, 1610, 1555, 1497/cm.
[α]D = +40,1° (MeOH, c = 1,00, 23°C).
Nr. 2a-193
CDCl3 300 MHz
0,95 (1H, d, J = 10,2 Hz), 1,10 und 1,22 (jeweils 3H, jeweils s), 1,53–2,49 (14H, m), 2,58 (3H, s), 4,21 (1H, m), 5,35–5,54 (2H, m), 6,15 (1H, d, J = 8,1 Hz), 6,52 (1H, dd, J = 1,8 und 3,6 Hz), 7,29 (1H, t, J = 3,6 Hz), 7,94 (1H, t, J = 1,8 Hz).
IR (CHCl3): 3516, 3450, 3410, 3152, 3027, 3015, 2925, 2871, 2670, 1732, 1648, 1574, 1509/cm.
[α]D = +45,0° (MeOH, c = 1,01, 25°C).
Nr. 2a-194
CDCl3 300 MHz
0,99 (1H, d, J = 10,2 Hz), 1,11 und 1,24 (jeweils 3H, jeweils s), 1,52–2,53 (14H, m), 4,34 (1H, m), 5,33–5,57 (2H, m), 6,21 (1H, d, J = 8,6 Hz), 7,35–7,50 (2H, m), 7,83 (1H, s), 7,86 (1H, m), 8,31 (1H, m).
IR (CHCl3): 3443, 3067, 3013, 2925, 2870, 2665, 1708, 1651, 1515, 1493/cm.
[α]D = +55,7° (MeOH, c = 1,01, 23°C).
Nr. 2a-195
CDCl3 300 MHz
1,01 (1H, d, J = 10,0 Hz), 1,06 und 1,26 (jeweils 3H, jeweils s), 1,50–2,64 (14H, m), 2,68 (3H, s), 4,40 (1H, m), 5,36–5,61 (2H, m), 6,02 (1H, d, J = 9,4 Hz), 7,30–7,42 (2H, m), 7,73–7,86 (2H, m).
IR (CHCl3): 3510, 3434, 3062, 3029, 3014, 2924, 2871, 2669, 1708, 1650, 1563, 1539, 1500/cm.
[α]D = +72,4° (MeOH, c = 1,00, 23°C).
Schmp. 111,0–112,0°C.
Nr. 2a-196
CDCl3 300 MHz
0,42 und 1,04 (jeweils 3H, jeweils s), 0,80 (1H, d, J = 10,0 Hz), 1,11–2,48 (14H, m), 2,24 (3H, s), 4,02 (1H, m), 5,23–5,44 (2H, m), 5,53 (1H, d, J = 8,8 Hz), 7,27–7,31 (2H, m), 7,42–7,48 (3H, m), 7,93 (1H, s).
IR (CHCl3): 3419, 3114, 3025, 3006, 2924, 2871, 2662, 1737, 1709, 1636, 1540, 1519/cm.
[α]D = +43,7° (MeOH, c = 1,01, 23°C).
Nr. 2a-197
CDCl3 300 MHz
0,95 (1H, d, J = 10,0 Hz), 1,09 und 1,23 (jeweils 3H, jeweils s), 1,54–2,46 (18H, m), 2,77 (4H, br), 4,21 (1H, m), 5,32–5,54 (2H, m), 6,02 (1H, d, J = 8,6 Hz), 7,43 (1H, s).
IR (CHCl3): 3445, 3101, 3024, 3014, 2928, 2865, 2661, 1739, 1708, 1646, 1550, 1507/cm.
[α]D = +51,9° (MeOH, c = 1,01, 23°C).
Nr. 2a-198
CDCl3 300 MHz
0,96 (1H, d, J = 10,2 Hz), 1,11 und 1,22 (jeweils 3H, jeweils s), 1,50–2,44 (14H, m), 4,24 (1H, m), 4,42 (2H, s), 5,35–5,49 (2H, m), 6,25 (1H, d, J = 8,1 Hz), 7,33 (1H, m), 7,43 (1H, dd, J = 1,5 und 7,5 Hz), 7,49 (1H, d, J = 8,1 Hz), 7,60–7,63 (1H, m), 7,68 (1H, dd, J = 1,8 und 7,8 Hz), 8,02 (1H, d, J = 1,8 Hz), 8,19 (1H, dd, J = 1,5 und 8,1 Hz).
IR (CHCl3): 3448, 3030, 3012, 2925, 2870, 1739, 1708, 1671, 1588, 1559, 1514, 1472/cm.
[α]D = +56,9° (MeOH, c = 1,01, 24°C).
Nr. 2a-199
CDCl3 300 MHz
0,96 (1H, d, J = 10,2 Hz), 1,11 und 1,22 (jeweils 3H, jeweils s), 1,51–2,46 (14H, m), 3,40 (1H, m), 3,76 (1H, m), 4,24 (1H, m), 5,33–5,51 (3H, m), 6,25 (1H, m), 7,16 (1H, m), 7,24–7,33 (2H, m), 7,46 (1H, d, J = 7,5 Hz), 7,52–7,60 (2H, m), 7,85 (1H, dd, J = 1,8 und 4, 5 Hz).
IR (CHCl3): 3583, 3447, 3062, 3028, 3013, 2924, 2871, 2663, 1708, 1651, 1600, 1557, 1514, 1471/cm.
[α]D = +54,8° (MeOH, c = 1,00, 23°C).
Nr. 2a-200
CDCl3 300 MHz
0,96 (1H, d, J = 10,2 Hz), 1,12 und 1,23 (jeweils 3H, jeweils s), 1,51–2,46 (14H, m), 4,25 (1H, m), 5,34–5,51 (2H, m), 6,25 (1H, d, J = 8,4 Hz), 7,02 und 7,10 (jeweils 1H, jeweils d, J = 12,3 Hz), 7,23–7,33 (4H, m), 7,50 (1H, m), 7,64 (1H, dd, J = 1,8 und 7,8 Hz), 7,82 (1H, d, J = 1,8 Hz).
IR (CHCl3): 3450, 3060, 3025, 3014, 2925, 2871, 2662, 1708, 1653, 1596, 1542, 1513, 1473/cm.
[α]D = +62,5° (MeOH, c = 1,00, 24°C).
Nr. 2a-201
CDCl3 300 MHz
0,95 (1H, d, J = 9,9 Hz), 1,15 und 1,22 (jeweils 3H, jeweils s), 1,55–2,60 (14H, m), 4,26 (1H, m), 5,35–5,63 (2H, m), 7,14 (1H, d, J = 9,9 Hz), 7,34 und 7,40 (jeweils 1H, jeweils d, J = 12,9 Hz), 7,62–7,73 (4H, m), 8,25–8,30 (2H, m), 8,72 (1H, d, J = 1,5 Hz).
IR (CHCl3): 3443, 3389, 3297, 3061, 3030, 3016, 2925, 2870, 1726, 1708, 1652, 1603, 1521, 1483, 1472, 1309/cm.
[α]D = +61,1° (MeOH, c = 1,01, 23°C).
Nr. 2a-202
CDCl3 300 MHz
0,96 (1H, d, J = 10,2 Hz), 1,09 und 1,22 (jeweils 3H, jeweils s), 1,52–2,43 (14H, m), 2,63 (3H, s), 4,25 (1H, m), 5,33–5,49 (2H, m), 6,19 (1H, d, J = 8,4 Hz), 7,10 und 7,58 (jeweils 2H, jeweils d, J = 9,0 Hz), 7,21 (1H, m), 7,30–7,32 (2H, m), 7,46 (1H, d, J = 7,5 Hz).
IR (CHCl3): 3511, 3453, 3062, 3032, 3014, 2925, 2870, 1739, 1708, 1650, 1595, 1556, 1516, 1482, 1471/cm.
[α]D = +60,2° (MeOH, c = 1,01, 25°C).
Nr. 2a-203
CDCl3 300 MHz
0,96 (1H, d, J = 10,5 Hz), 1,09 und 1,23 (jeweils 3H, jeweils s), 1,52–2,43 (14H, m), 4,23 (1H, m), 5,35–5,51 (2H, m), 5,93 (1H, d, 8,7 Hz), 6,56 (1H, dd, J = 0,9 und 1,8 Hz), 7,43 (1H, t, J = 1,8 Hz), 7,92 (1H, dd, J = 0,9 und 1,8 Hz).
IR (CHCl3): 3517, 3450, 3134, 3031, 3008, 2925, 2870, 2667, 1708, 1656, 1588, 1570, 1514/cm.
[α]D = +46,7° (MeOH, c = 0,92, 25°C).
Nr. 2b-1
[α]D = +25,6° (MeOH, c = 1,01, 23°C).
Nr. 2b-2
[α]D = +38,9° (MeOH, c = 1,01, 24°C).
Nr. 2c-1
[α]D = +60,5° (MeOH, c = 1,01, 22°C).
Nr. 2c-2
[α]D = +55,8° (MeOH, c = 0,92, 22°C).
Nr. 2c-3
[α]D = +54,7° (MeOH, c = 1,01, 22°C).
Nr. 2d-1
[α]D = –6,2° (MeOH, c = 1,00, 21°C).
Nr. 2d-2
[α]D = +15,8° (MeOH, c = 0,34, 22°C).
Nr. 2d-3
[α]D = +31,6° (MeOH, c = 1,01, 22°C).
Nr. 2e-1
[α]D = –9,4° (MeOH, c = 1,00, 22°C).
Nr. 2e-2
[α]D = –1,8° (MeOH, c = 1,02, 23°C).
Nr. 2e-3
[α]D = –6,7° (MeOH, c = 1,01, 23°C).
Nr. 2f-1
[α]D = +6,8° (MeOH, c = 1,01, 23°C).
Nr. 2f-2
[α]D = –2,6° (MeOH, c = 1,00, 22°C).
Nr. 2f-3
[α]D = –3,5° (MeOH, c = 1,01, 22°C).
Nr. 2g-1
[α]D = +54,6° (MeOH, c = 1,01, 24°C).Physicochemical properties of the above compounds are shown below. The following connection number corresponds to that described in the above tables.
No. 1k-1
[Α] D = -25.4 ° (CH 2 Cl 2 3 , c = 1.08, 23 ° C).
No. 1k-2
CDCl 3 200 MHz
1.07-2.28 (14H, m), 2.32 (2H, t, J = 7.4Hz), 2.63 (1H, m), 3.63 (3H, s), 3.93 (1H, m), 5.30-5.52 (2H, m), 6.35 (1H, d, J = 7.0 Hz), 7.48-7.60 (3H, m), 7, 88-8.02 (6H, m).
IR (CH 2 Cl 2 3 ): 3438, 3002, 2946, 2868, 1727, 1652, 1514, 1485, 1363, 1310, 1245, 1154 / cm.
[Α] D = -80.4 ° (CH 2 Cl 2 3 , c = 1.01, 24.0 ° C).
No. 1k-3
CDCl 3 200 MHz
1.10-2.26 (14H, m), 2.37 (2H, t, J = 7.2Hz), 2.60 (1H, m), 3.93 (1H, m), 5.30 -5.50 (2H, m), 6.33 (1H, d, J = 7.5 Hz), 7.48-7.58 (3H, m) 7.88 No. (6H, m).
IR (CH 2 Cl 2 3 ): 3446, 3004, 2952, 2874, 1709, 1652, 1515, 1485, 1305, 1153 / cm.
[Α] D = -96.4 ° (CH 2 Cl 2 3 , c = 1.05, 23.0 ° C).
No. 1k-4
CDCl 3 300 MHz
1.05-2.17 (14H, m), 2.38 (2H, t, J = 7.2Hz), 2.52 (1H, m), 3.81 (1H, m), 5.33 -5.50 (2H, m), 6.08 (1H, d, J = 7.6 Hz), 7.39-7.53 (3H, m), 7.57-7.62 (6H, m ).
IR (CH 2 Cl 2 3 ): 3420, 3250, 3008, 2948, 2870, 2660, 2208, 1735 (sh), 1705, 1640, 1500 / cm.
[Α] D = -21.9 ± 0.6 ° (CHCl 3 , c = 1.02, 22 ° C).
No. 1k-5
CDCl 3 300 MHz
1.05-2.14 (14H, m), 2.38 (2H, t, J = 7.2Hz), 2.51 (1H, m), 3.81 (1H, m), 5.34 -5.46 (2H, m), 6.07 (1H, d, J = 7.6 Hz), 7.33-7.56 (5H, m).
IR (CH 2 Cl 2 3 ): 3422, 3250, 3010, 2950, 2876, 2664, 2558, 2210, 1735 (sh), 1705, 1645, 1502, 1441, 1410, 1307, 1276 / cm.
[Α] D = -63.6 ± 1.9 ° (CHCl 3 , c = 0.56, 22 ° C).
No. 1k-6
CDCl 3 300 MHz
1.04-2.24 (14H, m), 2.36 (2H, t, J = 7.5Hz), 2.58 (1H, m), 3.88 (1H, m), 5.30 -5.43 (2H, m), 6.21 (1H, d, J = 7.2Hz), 7.41-7.49 (3H, m), 7.73-7.77 (2H, m ).
IR (CH 2 Cl 2 3 ): 3447, 3011, 2955, 1708, 1653, 1603, 1578, 1515, 1486, 1457, 1312, 1211, 1164 / cm.
[Α] D = -60.3 ° (CH 2 Cl 2 3 , c = 1.00, 23 ° C).
No. 1k-7
CDCl 3 300 MHz
1.04-2.22 (14H, m), 2.36 (2H, t, J = 7.2Hz), 2.57 (1H, m), 3.87 (1H, m), 5.30 -5.44 (2H, m), 6.17 (1H, d, 8.7Hz), 6.99-7.40 (7H, m), 7.73 (2H, d, J = 7.5 Hz).
IR (CH 2 Cl 2 3 ): 3449, 3013, 2955, 1739, 1708, 1651, 1609, 1588, 1522, 1487, 1243, 1227, 1169 / cm.
[Α] D = -60.2 ° (CH 2 Cl 2 3 , c = 0.92, 23 ° C).
No. 1k-8
CDCl 3 300 MHz
1.04-2.25 (14H, m), 2.34 (2H, t, J = 7.5Hz), 2.56 (1H, m), 3.87 (1H, m), 5.30 -5.44 (2H, m), 6.19 (1H, d, J = 7.5 Hz), 6.83-6.94 (6H, m), 7.69 (2H, d, 8.7 Hz).
IR (CH 2 Cl 2 3 ): 3599, 3455, 3012, 2955, 1711, 1644, 1604, 1577, 1524, 1507, 1492, 1290, 1236, 1197, 1170 / cm.
[Α] D = -47.7 ° (CH 2 Cl 2 3 , c = 1.01, 22 ° C).
No. 1k-9
CDCl 3 300 MHz
1.04-2.20 (14H, m), 2.31 (3H, s), 2.36 (2H, t, J = 7.2Hz), 2.56 (1H, m), 3.86 (1H, m), 5.30-5.43 (2H, m), 6.16 (1H, d, J = 7.2Hz), 7.00-7.11 (6H, m), 7, 74 (2H, d, 8.7 Hz).
IR (CH 2 Cl 2 3 ): 3450, 3010, 2955, 1750, 1709, 1651, 1609, 1596, 1523, 1489, 1370, 1247, 1227, 1183 / cm.
[Α] D = -54.7 ° (CH 2 Cl 2 3 , c = 1.01, 22 ° C).
No. 1k-10
CDCl 3 300 MHz
1.04-2.22 (14H, m), 2.35 (2H, t, J = 7.2Hz), 2.56 (1H, m), 3.82 (3H, s), 3.86 (1H, m), 5.30-5.43 (2H, m), 6.17 (1H, d, J = 6.9 Hz), 6.89-7.01 (6H, m), 7, 70 (2H, d, 8.7 Hz).
IR (CH 2 Cl 2 3 ): 3023, 2955, 1742, 1708, 1649, 1613, 1602, 1577, 1522, 1507, 1490, 1227, 1210, 1170 / cm.
[Α] D = -58.1 ° (CHCl 3 , c = 1.01, 22 ° C).
No. 1m-1
CDCl 3 300 MHz
1.06-2.25 (14H, m), 2.32 (2H, t, J = 7.4Hz), 2.61 (1H, m), 3.63 (3H, s), 3.91 (1H, m), 5.33-5.47 (2H, m), 6.24 (1H, d, J = 6.9Hz), 7.35-7.38 (3H, m), 7, 53-7.60 (4H, m), 7.75-7.78 (2H, m).
IR (CH 2 Cl 2 3 ): 3438, 3008, 2946, 2875, 2212, 1732, 1650, 1605, 1519, 1496 / cm.
[Α] D = + 76 ° (CHCl 3 , c = 1.39, 24 ° C).
No. 1m-2
CDCl 3 300 MHz
1.05-2.20 (14H, m), 2.36 (2H, t, J = 6.2Hz), 2.59 (1H, m), 3.89 (1H, m), 5.29 -5.48 (2H, m), 6.26 (1H, d, J = 7.0 Hz), 7.26-7.38 (3H, m), 7.52-7.60 (4H, m ), 7.73-7.77 (2H, m).
IR (CH 2 Cl 2 3 ): 3444, 3012, 2952, 2874, 2664, 2214, 1718 (sh), 1708, 1649, 1605, 1520, 1498 / cm.
[Α] D = + 81.4 ° (CHCl 3 , c = 1.01, 23 ° C).
No. 1m-3
CDCl 3 300 MHz
1.06-2.23 (14H, m), 2.32 (2H, t, J = 7.0 Hz), 2.62 (1H, m), 3.63 (3H, s), 3.93 (1H, m), 5.30-5.50 (2H, m), 6.28 (1H, d, J = 7.0 Hz), 7.38-7.51 (3H, m), 7, 58, -7.67 (4H, m), 7.83-7.88 (2H, m).
IR (CH 2 Cl 2 3 ): 3438, 3008, 2948, 2875, 1783 (w), 1727, 1650, 1608, 1580 (w), 1523, 1501, 1482 / cm
[Α] D = + 59 ° (CH 2 Cl 2 3 , c = 1.49, 25 ° C).
No. 1m-4
CDCl 3 300 MHz
1.08-2.25 (14H, m), 2.36 (2H, t, J = 7.4Hz), 2.59 (1H, m), 3.91 (1H, m), 5.28 -5.48 (3H, m), 6.29 (1H, d, J = 7.4Hz), 7.38-7.50 (3H, m), 7.61-7.67 (4H, m ), 7.81-7.86 (2H, m).
IR (CH 2 Cl 2 3 ): 3436, 3010, 2948, 2868, 1727, 1715 (sh), 1649, 1615 (w), 1524, 1502, 1482, 1372 / cm.
[Α] D = + 72 ° (CHCl 3 , c = 0.98, 25 ° C).
No. 1m-5
CDCl 3 300 MHz
1.09-2.20 (14H, m), 2.32 (2H, t, J = 7.2Hz), 2.63 (1H, m), 3.63 (3H, s), 3.92 (1H, m), 5.31-5.51 (2H, m), 6.35 (1H, d, J = 7.0 Hz), 7.51-7.60 (3H, m), 7, 92-7.97 (6H, m).
IR (CH 2 Cl 2 3 ): 3436, 3008, 2946, 2875, 1727, 1652, 1608 (w), 1515, 1484 / cm.
[Α] D = + 82 ° (CHCl 3 , c = 0.99, 25 ° C).
No. 1m-6
CDCl 3 300 MHz
1.09-2.23 (14H, m), 2.37 (2H, t, J = 7.2Hz), 2.60 (1H, m), 3.92 (1H, m), 5.30 -5.49 (2H, m), 6.32 (1H, d, J = 7.4Hz), 7.51-7.55 (3H, m), 7.85-7.98 (6H, m ).
IR (CH 2 Cl 2 3 ): 3436, 3010, 2950, 2875, 2670, 1727, 1715 (sh), 1650, 1605 (w), 1515, 1484 / cm.
[Α] D = + 84 ° (CHCl 3 , c = 1.54, 25 ° C).
No. 1m-7
CDCl 3 300 MHz
1.03-2.18 (14H, m), 2.32 (2H, t, J = 7.4Hz), 2.59 (1H, m), 3.64 (3H, s), 3.89 (1H, m), 5.29-5.49 (2H, m), 6.16 (1H, d, J = 7.8 Hz), 6.98-7.06 (4H, m), 7, 14-7.20 (1H, m), 7.34-7.41 (2H, m), 7.73-7.78 (2H, m).
IR (CH 2 Cl 2 3 ): 3438, 3008, 2946, 2868, 1727, 1648, 1610, 1586, 1519, 1485 / cm.
[Α] D = + 54 ° (CHCl 3 , c = 1.29, 25 ° C).
No. 1m-8
CDCl 3 300 MHz
1.06-2.21 (14H, m), 2.36 (2H, t, J = 7.5Hz), 2.58 (1H, m), 3.88 (1H, m), 5.31 -5.46 (2H, m), 6.17 (1H, d, J = 6.9 Hz), 6.99-7.05 (4H, m), 7.15-7.21 (1H, m ), 7.36-7.41 (2H, m), 7.72-7.75 (2H, m).
IR (CH 2 Cl 2 3 ): 3436, 3010, 2948, 2868, 2675, 1730 (sh), 1709, 1647, 1608, 1586, 1520, 1485 / cm.
[Α] D = + 56 ° (CHCl 3 , c = 0.97, 25 ° C).
No. 1m-9
CDCl 3 300 MHz
1.05-2.18 (14H, m), 2.29-2.34 (5H, m), 2.59 (1H, m), 3.64 (3H, s), 3.89 (1H, m), 5.32-5.46 (2H, m), 6.16 (1H, d, J = 7.5Hz), 7.00-7.11 (6H, m), 7.74-7 , 77 (2H, m).
IR (CH 2 Cl 2 3 ): 3440, 3010, 2946, 2868, 1729, 1649, 1595, 1519, 1488 / cm.
[Α] D = + 47 ° (CHCl 3 , c = 0.82, 25 ° C).
No. 1m-10
CDCl 3 300 MHz
1.04-2.20 (14H, m), 2.31-2.39 (5H, m), 2.57 (1H, m), 3.87 (1H, m), 5.28-5, 47 (2H, m), 6.17 (1H, d, J = 7.0 Hz), 6.99-7.12 (6H, m), 7.72-7.76 (2H, m).
IR (CH 2 Cl 2 3 ): 3674, 3572, 3438, 3010, 2948, 2868, 2626, 1748, 1710, 1648, 1615, 1595, 1520, 1489 / cm.
[Α] D = + 51 ° (CHCl 3 , c = 0.91, 25 ° C).
No. 1m-11
CDCl 3 300 MHz
1.04-2.16 (14H, m), 2.31 (2H, t, J = 7.2Hz), 2.59 (1H, m), 3.63 (3H, s), 3.89 (1H, m), 5.29-5.49 (2H, m), 6.24 (1H, d, J = 7.4Hz), 6.54 (1H, s), 6.83-6, 93 (6H, m), 7.69-7.73 (2H, m).
IR (CH 2 Cl 2 3 ): 3674, 3588, 3438, 3296, 3010, 2946, 2868, 1725, 1646, 1603, 1520, 1504, 1489 / cm.
[Α] D = + 51 ° (CHCl 3 , c = 0.91, 25 ° C).
No. 1m-12
CDCl 3 300 MHz
1.04-2.21 (14H, m), 2.33 (2H, t, J = 8.0Hz), 2.56 (1H, m), 3.87 (1H, m), 5.28 -5.48 (2H, m), 6.23 (1H, d, J = 8.0 Hz), 6.75 (1H, m), 6.87-6.94 (6H, m), 7, 66-7.71 (2H, m), 9.63 (1H, br).
IR (CH 2 Cl 2 3 ): 3674, 3582, 3436, 3275, 3010, 2950, 2868, 2675, 1727, 1710 (sh), 1643, 1603, 1522, 1504, 1490 / cm.
[Α] D = + 30 ° (CHCl 3 , c = 0.97, 25 ° C).
No. 1m-13
CDCl 3 300 MHz
1.01-2.18 (14H, m), 2.31 (2H, t, J = 7.4Hz), 2.58 (1H, m), 3.63 (3H, s), 3.82 (3H, s), 3.89 (1H, m), 5.29-5.48 (2H, m), 6.14 (1H, d, J = 7.0Hz), 6.88-7, 02 (6H, m), 7.70-7.74 (2H, m).
IR (CH 2 Cl 2 3 ): 3442, 3402, 3004, 2946, 2868, 1727, 1648, 1600, 1518, 1499 / cm.
[Α] D = + 42 ° (CHCl 3 , c = 1.82, 26 ° C).
No. 1m-14
CDCl 3 300 MHz
1.05-2.21 (14H, m), 2.35 (2H, t, J = 7.2Hz), 2.55 (1H, m), 3.82 (3H, s), 3.88 (1H, m), 5.27-5.46 (2H, m), 6.16 (1H, d, J = 7.2Hz), 6.88-7.02 (6H, m), 7, 68-7.73 (2H, m).
IR (CH 2 Cl 2 3 ): 3438, 3012, 2948, 2870, 2650, 1730 (sh), 1709, 1647, 1615 (sh), 1601, 1519, 1492 / cm.
[Α] D = + 64 ° (CHCl 3 , c = 0.70, 25 ° C).
No. 1m-15
CDCl 3 300 MHz
1.05-2.20 (14H, m), 2.29-2.36 (5H, m), 2.62 (1H, m), 3.63 (3H, s), 3.92 (1H, m), 5.30-5.50 (2H, m), 6.25 (1H, d, J = 7.2Hz), 7.16-7.21 (2H, m), 7.59-7 , 64 (4H, m), 7.83-7.87 (2H, m).
IR (CH 2 Cl 2 3 ): 3446, 3010, 2946, 2868, 1745 (sh), 1728, 1650, 1615, 1525, 1507, 1486 / cm.
[Α] D = + 65.0 ° (CHCl 3 , c = 1.02, 23 ° C).
No. 1m-16
CDCl 3 300 MHz
1.08-2.21 (14H, m), 2.34-2.40 (5H, m), 2.59 (1H, m), 3.90 (1H, m), 5.29-5, 48 (2H, m), 6.29 (1H, d, J = 7.0 Hz), 7.18 (2H, d, J = 8.6 Hz), 7.58-7.64 (4H, m ), 7.83 (2H, d, J = 8.2 Hz).
IR (CH 2 Cl 2 3 ): 3438, 3012, 2948, 2870, 2622, 1749, 1710, 1649, 1610, 1526, 1508, 1487 / cm.
[Α] D = + 66 ° (CHCl 3 , c = 1.21, 24 ° C).
No. 1m-17
CDCl 3 300 MHz
1.06-2.19 (14H, m), 2.32 (2H, t, J = 7.2Hz), 2.62 (1H, m), 3.63 (3H, s), 3.93 (1H, m), 5.30-5.50 (2H, m), 6.32 (1H, d, J = 7.6 Hz), 6.41 (1H, s), 6.94 (2H, d, J = 9.0 Hz), 7.47 (2H, d, J = 9.0 Hz), 7.58 (2H, d, J = 8.6 Hz), 7.81 (2H, d, J = 8.6 Hz).
IR (CH 2 Cl 2 3 ): 3580, 3434, 3284, 3010, 2946, 2868, 1726, 1646, 1606, 1528, 1490 / cm.
[Α] D = + 62.4 ° (CHCl 3 , c = 1.01, 23 ° C).
No. 1m-18
CDCl 3 + CD 3 OD 300 MHz
1.11-2.18 (14H, m), 2.32 (2H, t, J = 7.4Hz), 2.59 (1H, m), 3.88 (1H, m), 5.30 -5.49 (2H, m), 6.55 (1H, d, J = 7.0 Hz), 6.92 (2H, d, J = 8.6 Hz), 7.47 (2H, d, J = 8.6 Hz), 7.59 (2H, d, J = 8.6 Hz), 7.79 (2H, d, J = 8.2 Hz).
IR (Nujol): 3398, 3175, 2725, 1696, 1635, 1601, 1531, 1510 / cm.
[Α] D = + 99.5 ° (CH 3 OH, c = 1.011, 25 ° C).
No. 1m-19
CDCl 3 300 MHz
1.05-2.20 (14H, m), 2.32 (2H, t, J = 7.4Hz), 2.61 (1H, m), 3.63 (3H, s), 3.86 (3H, s), 3.94 (1H, m), 5.30-5.50 (2H, m), 6.24 (1H, d, J = 7.0Hz), 6.99 (2H, d, J = 8.6 Hz), 7.53-7.63 (4H, m), 7.82 (2H, d, J = 8.6 Hz).
IR (CH 2 Cl 2 3 ): 3440, 3006, 2946, 2875, 1726, 1649, 1606, 1527, 1510, 1489 / cm.
[Α] D = + 68 ° (CHCl 3 , c = 0.88, 26 ° C).
No. 1m-20
CDCl 3 300 MHz
1.09-2.20 (14H, m), 2.35 (2H, t, J = 7.3Hz), 2.58 (1H, m), 3.85 (3H, s), 3.89 (1H, m), 5.28-5.48 (2H, m), 6.35 (1H, d, J = 7.2Hz), 6.98 (2H, d, J = 8.8Hz) , 7.51-7.61 (4H, m), 7.81 (2H, d, J = 8.4Hz), 8.34 (1H, br).
IR (CH 2 Cl 2 3 ): 3446, 3012, 2952, 2881, 2640, 1730 (sh), 1707, 1647, 1606, 1527, 1510, 1489 / cm.
[Α] D = + 83 ° (CHCl 3 , c = 1.00, 25 ° C).
No. 1m-21
CDCl 3 300 MHz
1.05-2.14 (14H, m), 2.37 (2H, t, J = 7.2Hz), 2.51 (1H, m), 3.81 (1H, m), 5.34 -5.46 (2H, m), 6.11 (1H, d, J = 7.5 Hz), 7.33-7.48 (3H, m), 7.53-7.55 (2H, m ).
IR (CH 2 Cl 2 3 ): 3420, 3250, 3008, 2948, 2870, 2660, 2210, 1735 (sh), 1705, 1645, 1503, 1441, 1409 / cm.
[Α] D = + 59.2 ± 1.0 ° (CHCl 3 , c = 1.023, 22 ° C).
No. 1m-22
CDCl 3 300 MHz
1.05-2.17 (14H, m), 2.37 (2H, t, J = 7.2Hz), 2.52 (1H, m), 3.82 (1H, m), 5.32 -5.47 (2H, m), 6.20 (1H, d, J = 7.6Hz), 7.38-7.53 (3H, m), 7.58-7.61 (6H, m ), 9.11 (1H, br).
IR (CH 2 Cl 2 3 ): 3420, 3250, 3010, 2984, 2870, 2675, 2208, 1730 (sh), 1705, 1640, 1500, 1406 / cm.
[Α] D = + 57.4 ° (CHCl 3 , c = 1.83, 23 ° C).
No. 1m-23
CDCl 3 300 MHz
1.05-2.18 (14H, m), 2.31 (2H, t, J = 7.5Hz), 2.60 (1H, m), 3.63 (3H, s), 3.90 (1H, m), 5.32-5.47 (2H, m), 6.22 (1H, d, J = 6.9 Hz), 7.40-7.49 (3H, m), 7, 76-7.79 (2H, m).
IR (CH 2 Cl 2 3 ): 3438, 3008, 2946, 2868, 1727, 1651, 1603, 1585, 1512, 1484 / cm.
[Α] D = + 52 ° (CHCl 3 , c = 1.49, 25 ° C).
No. 1m-24
CDCl 3 300 MHz
1.05-2.21 (14H, m), 2.36 (2H, t, J = 7.2Hz), 2.57 (1H, m), 3.89 (1H, m), 5.28 -5.47 (2H, m), 6.22 (1H, d, J = 7.0 Hz), 7.39-7.55 (3H, m), 7.73-7.79 (2H, m ).
IR (CH 2 Cl 2 3 ): 3676, 3572, 3436, 3010, 2948, 2875, 1730 (sh), 1709, 1650, 1600, 1580, 1514, 1484 / cm.
[Α] D = + 57 ° (CHCl 3 , c = 0.97, 26 ° C).
No. 1m-25
CDCl 3 300 MHz
1.04-2.18 (14H, m), 2.28-2.35 (5H, m), 2.59 (1H, m), 3.62 (3H, s), 3.88 (1H, m), 5.29-5.49 (2H, m), 6.20 (1H, d, J = 7.2 Hz), 7.15 (2H, d, J = 9.0 Hz), 7, 80 (2H, d, J = 8.8 Hz).
IR (CH 2 Cl 2 3 ): 3436, 3010, 2946, 2868, 1752, 1727, 1653, 1602, 1519, 1491 / cm.
[Α] D = + 53 ° (CHCl 3 , c = 1.63, 25 ° C).
No. 1m-26
CDCl 3 300 MHz
1.05-2.19 (14H, m), 2.32-2.38 (5H, m), 2.56 (1H, m), 3.88 (1H, m), 5.29-5, 47 (2H, m), 6.25 (1H, d, J = 7.4 Hz), 7.15 (2H, d, J = 9.0 Hz), 7.78 (2H, d, J = 8 , 6 Hz).
IR (CH 2 Cl 2 3 ): 3434, 3016, 3006, 2948, 2880, 2622, 1752, 1730 (sh), 1710, 1651, 1605, 1520, 1492 / cm.
[Α] D = + 58 ° (CHCl 3 , c = 3.68, 24 ° C).
No. 1m-27
CDCl 3 300 MHz
1.05-2.16 (14H, m), 2.30 (2H, t, J = 7.5Hz), 2.57 (1H, m), 3.62 (3H, s), 3.87 (1H, m), 5.27-5.47 (2H, m), 6.32 (1H, d, J = 7.4Hz), 6.85 (2H, d, J = 8.6Hz) , 7.62 (2H, d, J = 8.6 Hz), 8.35 (1H, s).
IR (CH 2 Cl 2 3 ): 3580, 3450, 3216, 3010, 2946, 2868, 1726, 1640, 1608, 1584, 1528, 1496 / cm.
[Α] D = + 56.2 ° (CHCl 3 , c = 0.713, 23 ° C).
No. 1m-28
CDCl 3 200 MHz
1.10-2.25 (14H, m), 2.32 (2H, t, J = 7.2Hz), 2.55 (1H, br), 3.82-3.93 (1H, m) , 5.27-5.47 (2H, m), 6.25 (1H, d, J = 7.4Hz), 6.86 (2H, d, J = 8.6Hz), 7.62 ( 2H, d, J = 8.6 Hz).
IR (CH 2 Cl 2 3 ): 3438, 3242, 2675, 1730 (sh), 1708, 1639, 1607, 1585 / cm.
No. 1m-29
CDCl 3 300 MHz
1.05-2.18 (14H, m), 2.31 (2H, t, J = 7.4Hz), 2.58 (1H, m), 3.64 (3H, s), 3.85 (3H, s), 3.89 (1H, m), 5.29-5.48 (2H, m), 6.14 (1H, d, J = 6.6Hz), 6.92 (2H, d, J = 9.0 Hz), 7.74 (2H, d, J = 9.0 Hz).
IR (CH 2 Cl 2 3 ): 3445, 3008, 2946, 2868, 1727, 1646, 1606, 1578, 1523, 1493 / cm.
[Α] D = + 53 ° (CHCl 3 , c = 2.03, 24 ° C).
No. 1m-30
CDCl 3 300 MHz
1.04-2.21 (14H, m), 2.36 (2H, t, J = 7.3Hz), 2.56 (1H, m), 3.85 (3H, s), 3.88 (1H, m), 5.27-5.46 (2H, m), 6.15 (1H, d, J = 7.2Hz), 6.92 (2H, d, J = 8.6Hz) , 7.73 (2H, d, J = 8.6 Hz) IR (CHCl 3 ): 3440, 3010, 2950, 2870, 2645, 1727, 1710 (sh), 1646, 1606, 1575, 1524, 1494 / cm.
[Α] D = + 62 ° (CH 2 Cl 2 3 , c = 1.10, 24 ° C).
No. 1m-31
CDCl 3 + CD 3 OD 300 MHz
1.16-2.20 (14H, m), 2.31 (2H, t, J = 7.2Hz), 2.59 (1H, m), 3.85 (1H, m), 5.31 -5.51 (2H, m), 7.13-7.21 (1H, m), 7.31-7.42 (2H, m), 7.68-7.93 (6H, m).
IR (Nujol): 3344, 3175, 2715, 2675, 1699, 1631, 1566 / cm.
[Α] D = + 67 ° (CH 3 OH, c = 1.01, 24 ° C).
No. 1m-32
CDCl 3 200 MHz
1.09-2.23 (14H, m), 2.33 (2H, t, J = 7.1Hz), 2.57 (1H, br), 3.40-3.93 (9H, m) , 4.41 (1H, br), 5.29-5.48 (2H, m), 6.44 (1H, d, J = 7.4Hz), 7.43 (2H, d, J = 8 , 2 Hz), 7.80 (2H, d, J = 7.8 Hz).
IR (CH 2 Cl 2 3 ): 3434, 3354, 1726, 1720 (sh), 1660 (sh), 1626 / cm.
No. 1m-33
CDCl 3 200 MHz
1.14-2.25 (14H, m), 2.37 (2H, t, J = 7.3Hz), 2.64 (1H, br), 3.93-4.01 (1H, m) , 5.30-5.51 (2H, m), 6.47 (1H, d, J = 7.4Hz), 7.63-7.74 (2H, m), 7.79 (2H, s ), 7.89-7.93 (1H, m), 8.00 (1H, dd, J = 2.3, 1.0 Hz), 8.30 (1H, d, J = 1.0 Hz) , 8.65-8.73 (2H, m).
IR (CH 2 Cl 2 3 ): 3450, 2675, 1728, 1707, 1649, 1528, 1509 / cm.
[Α] D = + 82.8 ± 1.2 ° (CHCl 3 , c = 1.01, 23 ° C).
No. 2a-1
[Α] D = + 69.0 ° (MeOH, c = 1.01, 25 ° C).
No. 2a-2
CDCl 3 300 MHz
0.99 (1H, d, J = 10.2 Hz), 1.15 and 1.24 (each 3H, each s), 1.50-2.50 (14H, m), 4.30 (1H, m), 5.35-5.52 (2H, m), 6.32 (1H, d, 8.7Hz), 7.36-7.49 (3H, m), 7.58-7.62 (2H, m), 7.66 and 7.80 (each 2H, each d, 8.7 Hz).
IR (CH 2 Cl 2 3 ): 3116, 3014, 2925, 2870, 2663, 1708, 1651, 1610, 1524, 1504, 1484, 1472 / cm.
[Α] D = + 64.1 ° (MeOH, c = 1.02, 25 ° C).
No. 2a-3
[Α] D = + 76.6 ° (MeOH, c = 1.18, 26 ° C).
No. 2a-4
CDCl 3 300 MHz
0.99 (1H, d, J = 10.2Hz), 1.15 and 1.25 (each 3H, each s), 1.64-2.51 (14H, m), 4.31 (1H, m), 5.36-5.53 (2H, m), 6.33 (1H, d, J = 8.4Hz), 7.50-7.56 (3H, m), 7.85-7 , 98 (6H, m).
IR (CH 2 Cl 2 3 ): 3515, 3452, 3014, 2925, 2870, 1740, 1708, 1654, 1517, 1486, 1470 / cm.
[Α] D = + 79.5 ° (MeOH, c = 1.18, 22 ° C).
No. 2a-5
CD 3 OD 300 MHz
0.98 (1H, d, J = 9.9Hz), 1.18 and 1.25 (each 3H, each s), 1.56-1.71 (3H, m), 1.98-2, 40 (11H, m), 4.17 (1H, m), 5.41-5.52 (2H, m), 7.52-7.61 (3H, m), 7.91-8.01 ( 6H, m),
IR (KBr): 3416, 3063, 2983, 2921, 2869, 1704, 1643, 1566, 1518, 1488, 1408 / cm.
[Α] D = + 62.0 ° (MeOH, c = 1.00, 25 ° C).
No. 2a-6
[Α] D = + 64.1 ° (MeOH, c = 1.01, 25 ° C).
No. 2a-7
[Α] D = + 65.3 ° (MeOH, c = 0.99, 25 ° C).
No. 2a-8
[Α] D = + 74.0 ° (MeOH, c = 1.01, 25 ° C).
No. 2a-9
[Α] D = + 71.0 ° (MeOH, c = 1.10, 25 ° C).
No. 2a-10
[Α] D = + 74.7 ° (MeOH, c = 1.00, 25 ° C).
No. 2a-11
[Α] D = + 72.1 ° (MeOH, c = 1.00, 25 ° C).
No. 2a-12
[Α] D = + 53.1 ° (CH 2 Cl 2 3 , c = 1.01, 26 ° C).
Mp 155.0-156.0 ° C.
No. 2a-13
CDCl 3 300 MHz
0.98 (1H, d, J = 10.2Hz), 1.18 and 1.25 (each 3H, each s), 1.63-2.40 (14H, m), 4.30 (1H, m), 5.46-5.58 (2H, m), 6.44 (1H, d, J = 8.4Hz), 7.49 and 7.77 (2H each, each d, 8.7Hz ), 7.54 (1H, s).
IR (CH 2 Cl 2 3 ): 3689, 3378, 3028, 3014, 2924, 1713, 1652, 1602, 1522, 1496 / cm.
[Α] D = + 78.3 ° (MeOH, c = 0.84, 25 ° C).
Mp. 205.0-206.0 ° C.
No. 2a-14
[Α] D = + 72.5 ° (MeOH, c = 1.07, 25 ° C).
No. 2a-15
CDCl 3 300 MHz
0.99 (1H, d, J = 9.9 Hz), 1.14 and 1.24 (each 3H, each s), 1.55-2.44 (14H, m), 4.27 (1H, m), 5.30-5.50 (2H, m), 6.29 (1H, d, J = 9.0 Hz), 7.11 and 7.20 (each 1H, each d, J = 16, 2 Hz), 7.29-7.55 (5H, m), 7.57 and 7.72 (each 2H, each d, 8.7 Hz).
IR (CH 2 Cl 2 3 ): 3453, 3083, 3022, 3013, 2925, 2870, 1708, 1650, 1607, 1560, 1522, 1496 / cm.
[Α] D = + 72.3 ° (MeOH, c = 1.00, 27 ° C).
Mp. 115.0-117.0 ° C.
No. 2a-16
CDCl 3 300 MHz
0.92 (1H, d, J = 10.2 Hz), 1.11 and 1.23 (each 3H, each s), 1.50-2.48 (14H, m), 3.62 (3H, s), 4.29 (1H, m), 5.30-5.50 (2H, m), 6.20 (1H, d, 8.7Hz), 6.59 and 6.68 (each 1H, each d, J = 12.3 Hz), 7.23 (5H, s), 7.29 and 7.59 (each 2H, each d, J = 8.1 Hz).
IR (CH 2 Cl 2 3 ): 3453, 3024, 3016, 2924, 2870, 1730, 1651, 1607, 1520, 1495 / cm.
[Α] D = + 56.8 ° (MeOH, c = 1.04, 24 ° C).
No. 2a-17
CDCl 3 300 MHz
0.97 (1H, d, J = 10.2Hz), 1.11 and 1.23 (each 3H, each s), 1.50-2.38 (14H, m), 4.26 (1H, m), 5.30-5.50 (2H, m), 6.23 (1H, d, J = 8.4 Hz), 6.59 and 6.70 (each 1H, each d, J = 12, 3 Hz), 7.23 (5H, s), 7.30 and 7.57 (each 2H, each d, 8.7 Hz).
IR (CH 2 Cl 2 3 ): 3452, 3081, 3019, 3014, 2925, 2870, 2665, 1708, 1650, 1607, 1521, 1495 / cm.
[Α] D = + 61.6 ° (MeOH, c = 1.00, 27 ° C).
No. 2a-18
CDCl 3 300 MHz
0.97 (1H, d, J = 10.2 Hz), 1.11 and 1.23 (each 3H, each s), 1.50-2.50 (14H, m), 3.61 (3H, s), 4.31 (1H, m), 5.35-5.51 (2H, m), 6.33 (1H, d, J = 8.4Hz), 7.48-7.64 (4H , m), 7.79-7.83 (2H, m), 7.91 (1H, dt, J = 1.5 and 7.8 Hz), 8.01 (1H, dt, J = 1.5 and 7.8 Hz), 8.13 (1H, t, J = 1.5 Hz).
IR (CH 2 Cl 2 3 ): 3450, 3026, 3013, 2925, 2870, 1730, 1659, 1600, 1510 / cm.
[Α] D = + 56.0 ° (MeOH, c = 1.01, 25 ° C).
No. 2a-19
CDCl 3 300 MHz
0.95 (1H, d, J = 9.9Hz), 1.14 and 1.21 (each 3H, each s), 1.53-2.60 (14H, m), 4.25 (1H, m), 5.35-5.64 (2H, m), 7.21 (1H, d, J = 7.8Hz), 7.49-7.68 (4H, m), 7.76-7 , 84 (3H, m), 8.25 (1H, m), 8.43 (1H, m).
IR (CH 2 Cl 2 3 ): 3382, 3196, 3025, 3015, 2925, 2870, 1725, 1652, 1599, 1577, 1521 / cm.
[Α] D = + 55.9 ° (MeOH, c = 1.00, 25 ° C).
No. 2a-20
CDCl 3 300 MHz
0.98 (1H, d, J = 10.2 Hz), 1.13 and 1.24 (each 3H, each s), 1.50-2.50 (14H, m), 3.62 (3H, s), 4.31 (1H, m), 5.35-5.51 (2H, m), 6.24 (1H, d, J = 8.4Hz), 7.40-7.52 (3H , m), 7.71-7.76 (2H, m).
IR (CH 2 Cl 2 3 ): 3453, 3025, 3013, 2925, 2870, 1730, 1753, 1579, 1514, 1486 / cm.
[Α] D = + 61.2 ° (MeOH, c = 1.04, 25 ° C).
No. 2a-21
CDCl 3 300 MHz
0.98 (1H, d, J = 10.2 Hz), 1.13 and 1.23 (each 3H, each s), 1.52-2.50 (14H, m), 4.28 (1H, m), 5.34-5.51 (2H, m), 6.27 (1H, d, 8.7Hz), 7.41-7.53 (3H, m), 7.71-7.74 (2H, m).
IR (CH 2 Cl 2 3 ): 3452, 3063, 3027, 3014, 2925, 2871, 1708, 1652, 1578, 1515, 1486 / cm.
[Α] D = + 62.0 ° (MeOH, c = 1.01, 27 ° C).
No. 2a-22
d 6 -DMSO 300 MHz
0.86 (1H, d, J = 9.9Hz), 1.10 and 1.16 (each 3H, each s), 1.42-1.52 (3H, m), 1.85-2, 46 (11H, m), 3.98 (1H, m), 5.32-5.43 (2H, m), 7.41 (3H, m), 7.88 (2H, d, J = 6, 6 Hz), 8.19 (1H, d, J = 6.6 Hz).
IR (KBr): 3367, 3060, 2984, 2922, 2868, 1634, 1563, 1529, 1487 / cm.
[Α] D = + 47.7 ° (MeOH, c = 1.00, 25 ° C).
No. 2a-23
[Α] D = + 62.7 ° (MeOH, c = 1.01, 27 ° C).
No. 2a-24
CDCl 3 300 MHz
0.99 (1H, d, J = 10.2 Hz), 1.14 and 1.25 (each 3H, each s), 1.52-2.50 (14H, m), 4.31 (1H, m), 5.36-5.52 (2H, m), 6.34 (1H, d, J = 8.4Hz), 7.47-7.52 (2H, m), 7.59-7 , 64 (1H, m), 7.78-7.83 (6H, m).
IR (CH 2 Cl 2 3 ): 3449, 3027, 3013, 2925, 2869, 1708, 1656, 1599, 1518, 1493 / cm.
[Α] D = + 63.1 ° (MeOH, c = 1.00, 25 ° C).
No. 2a-25
[Α] D = + 35.1 ° (MeOH, c = 1.00, 25 ° C).
No. 2a-26
[Α] D = + 35.5 ° (MeOH, c = 1.02, 25 ° C).
No. 2a-27
CDCl 3 300 MHz
0.97 (1H, d, J = 10.2 Hz), 1.12 and 1.23 (each 3H, each s), 1.52-2.50 (14H, m), 3.63 (3H, s), 4.29 (1H, m), 5.36-5.51 (2H, m), 6.18 (1H, d, J = 8.4Hz), 7.01 and 7.71 (each 2H, each d, 8.7 Hz,), 6.98-7.05 (2H, m), 7.16 (1H, t, J = 7.5 Hz), 7.34-7.41 (2H , m).
IR (CH 2 Cl 2 3 ): 3455, 3024, 3016, 2924, 2870, 1730, 1651, 1588, 1520, 1487 / cm.
[Α] D = + 56.4 ° (MeOH, c = 1.01, 25 ° C).
No. 2a-28
CDCl 3 300 MHz
0.98 (1H, d, J = 10.2 Hz), 1.12 and 1.23 (each 3H, each s), 1.52-2.50 (14H, m), 4.26 (1H, m), 5.34-5.51 (2H, m), 6.20 (1H, d, J = 9.0 Hz), 7.01 and 7.70 (each 2H, each d, J = 9, 0 Hz,), 6.98-7.15 (2H, m), 7.17 (1H, t, J = 7.5 Hz), 7.34-7.40 (2H, m).
IR (CH 2 Cl 2 3 ): 3454, 3031, 3018, 2925, 2870, 1708, 1650, 1588, 1523, 1487 / cm.
[Α] D = + 56.2 ° (MeOH, c = 1.00, 25 ° C).
No. 2a-29
[Α] D = + 53.0 ° (MeOH, c = 1.03, 25 ° C).
No. 2a-30
CDCl 3 300 MHz
0.97 (1H, d, J = 10.2 Hz), 1.10 and 1.23 (each 3H, each s), 1.52-2.50 (14H, m), 4.25 (1H, m), 5.30-5.50 (2H, m), 6.23 (1H, d, 8.7Hz), 6.36 (1H, s), 7.26-7.39 (10H, m ), 7.60 and 7.68 (each 2H, each d, J = 8.4 Hz).
IR (CH 2 Cl 2 3 ): 3451, 3088, 3064, 3029, 3014, 2925, 2869, 1707, 1652, 1522, 1495 / cm.
[Α] D = + 54.2 ° (MeOH, c = 1.00, 25 ° C).
No. 2a-31
CDCl 3 300 MHz
0.98 (1H, d, J = 10.2 Hz), 1.14 and 1.24 (each 3H, each s), 1.50-2.50 (14H, m), 3.63 (3H, s), 4.31 (1H, m), 5.30-5.50 (2H, m), 6.26 (1H, d, J = 8.4Hz), 6.90 (1H, t, J = 7.4 Hz), 7.13 (1H, d, 8.7 Hz), 7.29 (2H, t, J = 8.0 Hz), 7.67-7.75 (5H, m), 7.82 (1H, s).
IR (Nujol): 3380, 3244, 1723, 1638, 1601, 1578, 1535, 1495 / cm.
[Α] D = + 73.6 ° (MeOH, c = 0.50, 26 ° C).
Mp 133.0-134.0 ° C.
No. 2a-32
[Α] D = + 56.1 ° (MeOH, c = 1.02, 26 ° C).
No. 2a-33
CDCl 3 300 MHz
0.95 (1H, d, J = 10.2Hz), 1.10 and 1.21 (each 3H, each s), 1.50-2.50 (14H, m), 4.25 (1H, m), 5.13 (2H, s), 5.30-5.70 (3H, m), 6.41 (1H, d, J = 8.2 Hz), 6.89 (1H, s); 7.09 (1H, s), 7.17 and 7.72 (each 2H, each d, J = 8.2 Hz), 7.62 (1H, s).
IR (CH 2 Cl 2 3 ): 3450, 3125, 3031, 3013, 2925, 2870, 2467, 1917, 1708, 1654, 1615, 1575, 1523, 1497 / cm.
[Α] D = + 55.2 ° (MeOH, c = 1.01, 26 ° C).
No. 2a-34
[Α] D = + 72.9 ° (MeOH, c = 1.03, 25 ° C).
No. 2a-35
CDCl 3 300 MHz
0.98 (1H, d, J = 10.2Hz), 1.13 and 1.24 (each 3H, each s), 1.52-2.48 (14H, m), 4.28 (1H, m), 5.35-5.51 (2H, m), 6.28 (1H, d, 8.7Hz), 7.34-7.37 (3H, m), 7.52-7.55 (2H, m), 7.58 and 7.71 (each 2H, each d, 8.7 Hz).
IR (CH 2 Cl 2 3 ): 3515, 3452, 3030, 3012, 2925, 2870, 1739, 1708, 1652, 1607, 1555, 1521, 1497 / cm.
[Α] D = + 74.3 ° (MeOH, c = 1.01, 25 ° C).
No. 2a-36
[Α] D = + 23.4 ° (MeOH, c = 1.07, 25 ° C).
No. 2a-37
CDCl 3 300 MHz
0.83 (1H, d, J = 10.5 Hz), 0.95 and 1.18 (each 3H, each s), 1.44-2.46 (14H, m), 3.92 (1H, m), 5.34-5.52 (3H, m), 7.26-7.54 (9H, m), 7.62 (1H, s).
IR (CH 2 Cl 2 3 ): 3432, 3310, 3189, 3023, 3014, 2924, 2870, 1704, 1610, 1594, 1523, 1487 / cm.
[Α] D = + 25.3 ° (MeOH, c = 1.00, 26 ° C).
No. 2a-38
[Α] D = + 70.9 ° (MeOH, c = 1.02, 25 ° C).
No. 2a-39
[Α] D = + 70.6 ° (MeOH, c = 1.01, 25 ° C).
No. 2a-40
[Α] D = + 74.7 ° (MeOH, c = 1.00, 25 ° C).
No. 2a-41
[Α] D = + 72.1 ° (MeOH, c = 1.01, 24 ° C).
No. 2a-42
[Α] D = + 69.2 ° (MeOH, c = 1.00, 25 ° C).
No. 2a-43
[Α] D = + 70.8 ° (MeOH, c = 1.00, 25 ° C).
No. 2a-44
[Α] D = + 60.4 ° (MeOH, c = 1.00, 26 ° C).
No. 2a-45
CDCl 3 300 MHz
0.97 (1H, d, J = 9.9 Hz), 1.13 and 1.23 (each 3H, each s), 1.55-2.52 (14H, m), 4.29 (1H, m), 5.34-5.54 (2H, m), 6.33 (1H, d, J = 9.0 Hz), 7.10 (1H, t, J = 7.4 Hz), 7, 34 (2H, t, J = 7.4 Hz), 7.52 (2H, m), 7.68 and 7.75 (each 2H, each d, J = 8.4 Hz), 7.80 (1H , s), 8,10 (1H, s), 10,09 (1H, s).
IR (CH 2 Cl 2 3 ): 3393, 3195, 3093, 3033, 3013, 2925, 2870, 1698, 1656, 1598, 1537, 1498 / cm.
[Α] D = + 59.4 ° (MeOH, c = 1.01, 24 ° C).
No. 2a-46
[Α] D = + 63.5 ° (MeOH, c = 1.00, 25 ° C).
No. 2a-47
CDCl 3 300 MHz
0.97 (1H, d, J = 9.9 Hz), 1.12 and 1.23 (each 3H, each s), 1.54-2.48 (14H, m), 4.29 (1H, m), 5.35-5.52 (2H, m), 6.32 (1H, d, 8.7Hz), 7.26 (1H, m), 7.41 (2H, t, J = 7 , 8 Hz), 7.64 (2H, d, J = 7.5 Hz), 7.73 and 7.77 (each 2H, each d, J = 8.4 Hz), 7.95 (1H, s ), 9.20 (1H, s), 10.38 (1H, s).
IR (CH 2 Cl 2 3 ): 3450, 3339, 3003, 2992, 2925, 2870, 1706, 1653, 1596, 1523, 1495 / cm.
[Α] D = + 63.3 ° (MeOH, c = 1.00, 25 ° C).
No. 2a-48
[Α] D = + 63.8 ° (MeOH, c = 1.00, 24 ° C).
No. 2a-49
CDCl 3 300 MHz
1.00 (1H, d, J = 10.5 Hz), 1.17 and 1.26 (each 3H, each s), 1.55-2.52 (14H, m), 4.34 (1H, m), 5.36-5.54 (2H, m), 6.35 (1H, d, J = 9.0 Hz), 7.50-7.62 (3H, m), 7.90 and 8 , 33 (each 2H, each d, J = 8.4 Hz), 8.21 (2H, m)
IR (CH 2 Cl 2 3 ): 3451, 3029, 3022, 3016, 2925, 2870, 1708, 1655, 1542, 1508, 1498, 1471, 1459 / cm.
[Α] D = + 63.5 ° (MeOH, c = 1.02, 25 ° C).
Mp. 135.0-137.0 ° C.
No. 2a-50
[Α] D = + 68.9 ° (MeOH, c = 1.01, 24 ° C).
No. 2a-51
d 6 -DMSO 300 MHz
0.87 (1H, d, J = 9.9 Hz), 1.10 and 1.17 (each 3H, each s), 1.40-1.60 (3H, m), 1.90-2, 40 (11H, m), 3.98 (1H, m), 5.35-5.46 (2H, m), 7.64 (1H, s), 7.65 and 7.91 (each 2H, each d, 8.7 Hz), 8.06 (1H, d, J = 6.0 Hz), 9.32 (1H, br).
IR (KBr): 3385, 2962, 1734, 1707, 1632, 1529, 1498 / cm.
[Α] D = + 68.4 ° (MeOH, c = 1.01, 24 ° C).
No. 2a-52
[Α] D = + 76.2 ° (MeOH, c = 1.01, 24 ° C).
No. 2a-53
[Α] D = + 73.9 ° (MeOH, c = 1.02, 24 ° C).
No. 2a-54
[Α] D = + 68.1 ° (MeOH, c = 1.00, 24 ° C).
No. 2a-55
[Α] D = + 67.8 ° (MeOH, c = 1.00, 24 ° C).
No. 2a-56
[Α] D = + 65.4 ° (MeOH, c = 1.03, 25 ° C).
No. 2a-57
[Α] D = + 63.4 ° (MeOH, c = 1.01, 24 ° C).
No. 2a-58
[Α] D = + 66.6 ° (MeOH, c = 1.01, 24 ° C).
No. 2a-59
[Α] D = + 65.5 ° (MeOH, c = 1.00, 24 ° C).
No. 2a-60
[Α] D = + 60.9 ° (MeOH, c = 1.02, 25 ° C).
No. 2a-61
CDCl 3 300 MHz
0.97 (1H, d, J = 10.0 Hz), 1.10 and 1.22 (each 3H, each s), 1.50-2.50 (14H, m), 4.26 (1H, m), 5.30-5.54 (2H, m), 6.28 (1H, d, J = 8.6 Hz), 6.60 and 6.82 (each 1H, each d, J = 12, 4 Hz), 7.12 (2H, d, J = 6.0 Hz), 7.25 and 7.62 (each 2H, each d, J = 8.6 Hz), 8.47 (2H, d, J = 6.0 Hz).
IR (CH 2 Cl 2 3 ): 3452, 3027, 3019, 3013, 2925, 2870, 2980, 1708, 1651, 1606, 1520, 1494 / cm.
[Α] D = + 61.6 ° (MeOH, c = 1.01, 25 ° C).
No. 2a-62
[Α] D = + 72.0 ° (MeOH, c = 0.93, 25 ° C).
No. 2a-63
CDCl 3 300 MHz
0.99 (1H, d, J = 10.2 Hz), 1.14 and 1.24 (each 3H, each s), 1.50-2.50 (14H, m), 4.29 (1H, m), 5.36-5.55 (2H, m), 6.35 (1H, d, J = 9.1Hz), 7.04 and 7.27 (each 1H, each d, J = 16, 5 Hz), 7.37 (2H, d, J = 6.6 Hz), 7.56 and 7.76 (each 2H, each d, J = 8.4 Hz), 8.57 (2H, d, J = 6.6 Hz).
IR (CH 2 Cl 2 3 ): 3452, 3024, 3018, 3014, 2925, 2870, 2470, 1933, 1708, 1652, 1605, 1521, 1496 / cm.
[Α] D = + 69.2 ° (MeOH, c = 1.01, 25 ° C).
No. 2a-64
[Α] D = + 56.9 ° (MeOH, c = 1.24, 25 ° C).
No. 2a-65
CDCl 3 300 MHz
0.98 (1H, d, J = 10.5 Hz), 1.12 and 1.23 (each 3H, each s), 1.54-2.46 (14H, m), 4.27 (1H, m), 5.23 (2H, s), 5.34-5.52 (2H, m), 6.26 (1H, d, J = 8.4Hz), 7.32-7.45 (5H , m), 7.64 and 7.71 (each 2H, each d, J = 8.4 Hz), 8.15 (1H, s).
IR (CH 2 Cl 2 3 ): 3452, 3088, 3065, 3032, 3013, 2925, 2870, 1708, 1653, 1611, 1559, 1522, 1496 / cm.
[Α] D = + 61.0 ° (MeOH, c = 0.91, 25 ° C).
No. 2a-66
[Α] D = + 76.0 ° (MeOH, c = 1.01, 25 ° C).
No. 2a-67
CDCl 3 300 MHz
0.98 (1H, d, J = 10.4Hz), 1.14 and 1.24 (each 3H, each s), 1.54-2.46 (14H, m), 4.28 (1H, m), 5.32-5.53 (2H, m), 6.27 (1H, d, J = 8.6Hz), 6.92-7.31 (each 1H, each d, J = 16, 4 Hz), 7.02 (1H, dd, J = 5.8 and 3.6 Hz), 7.12 (1H, d, J = 3.6 Hz), 7.24 (1H, d, J = 5.8 Hz), 7.51 and 7.70 (each 2H, each d, J = 8.4 Hz).
IR (CH 2 Cl 2 3 ): 3453, 3029, 3013, 2925, 2870, 1739, 1650, 1604, 1524, 1515, 1494 / cm.
[Α] D = + 76.2 ° (MeOH, c = 1.00, 24 ° C).
Mp. 104.0-106.0 ° C.
No. 2a-68
[Α] D = + 57.7 ° (MeOH, c = 1.01, 25 ° C).
No. 2a-69
CDCl 3 300 MHz
0.99 (1H, d, J = 10.2Hz), 1.14 and 1.24 (each 3H, each s), 1.54-2.48 (14H, m), 4.28 (1H, m), 5.34-5.53 (2H, m), 6.29 (1H, d, J = 9.0 Hz), 6.54-6.74 (each 1H, each d, J = 12, 0 Hz), 7.02 (1H, dd, J = 4.8 and 3.3 Hz), 6.97 (1H, dd, J = 3.3 and 1.2 Hz), 7.13 (1H, dd, J = 4.8 and 1.2 Hz), 7.44 and 7.70 (2H each, each d, 8.7 Hz).
IR (CH 2 Cl 2 3 ): 3453, 3025, 3010, 2925, 2870, 1708, 1650, 1607, 1559, 1523, 1493 / cm.
[Α] D = + 58.4 ° (MeOH, c = 1.00, 25 ° C).
No. 2a-70
[Α] D = + 48.6 ° (MeOH, c = 1.00, 25 ° C).
No. 2a-71
CDCl 3 300 MHz
0.98 (1H, d, J = 10.2 Hz), 1.12 and 1.23 (each 3H, each s), 1.52-2.46 (14H, m), 2.31 (3H, s), 4.26 (1H, m), 5.33-5.52 (2H, m), 6.20 (1H, d, J = 9.3Hz), 7.02-7.11 (6H , m), 7.70 (2H, d, J = 9.0 Hz).
IR (CH 2 Cl 2 3 ): 3460, 3031, 3022, 3011, 2925, 2870, 1750, 1708, 1650, 1608, 1597, 1523, 1490 / cm.
[Α] D = + 48.9 ° (MeOH, c = 1.01, 25 ° C).
No. 2a-72
[Α] D = + 51.2 ° (MeOH, c = 1.02, 25 ° C).
No. 2a-73
CDCl 3 300 MHz
0.97 (1H, d, J = 9.9 Hz), 1.11 and 1.23 (each 3H, each s), 1.54-2.48 (14H, m), 4.27 (1H, m), 5.32-5.52 (2H, m), 6.24 (1H, d, J = 9.0 Hz), 6.83-6.94 (6H, m), 7.65 (2H , d, J = 9.0 Hz).
IR (CH 2 Cl 2 3 ): 3598, 3451, 3199, 3033, 3012, 2925, 2870, 1708, 1642, 1604, 1524, 1507, 1491 / cm.
[Α] D = + 52.2 ° (MeOH, c = 1.01, 25 ° C).
No. 2a-74
[Α] D = + 51.5 ° (MeOH, c = 0.92, 25 ° C).
No. 2a-75
CDCl 3 300 MHz
0.97 (1H, d, J = 10.2 Hz), 1.11 and 1.23 (each 3H, each s), 1.55-2.46 (14H, m), 3.82 (3H, s), 4.25 (1H, m), 5.32-5.52 (2H, m), 6.19 (1H, d, 8.7Hz), 6.89-7.01 (6H, m ), 7.65-7.68 (2H, m).
IR (CH 2 Cl 2 3 ): 3450, 3025, 3008, 2925, 2870, 2837, 1741, 1649, 1612, 1521, 1505, 1490 / cm.
[Α] D = + 51.1 ° (MeOH, c = 1.00, 25 ° C).
No. 2a-76
[Α] D = + 60.4 ° (MeOH, c = 0.98, 25 ° C).
No. 2a-77
CDCl 3 300 MHz
0.99 (1H, d, J = 10.5 Hz), 1.15 and 1.24 (each 3H, each s), 1.54-2.48 (14H, m), 2.34 (3H, s), 4.29 (1H, m), 5.32-5.54 (2H, m), 6.32 (1H, d, J = 8.4Hz), 7.19 and 7.60 (each 2H, each d, J = 8.4 Hz), 7.63 and 7.79 (each 2H, each d, J = 8.4 Hz).
IR (CH 2 Cl 2 3 ): 3452, 3027, 3012, 2925, 2870, 1751, 1709, 1651, 1611, 1560, 1527, 1509, 1489 / cm.
[Α] D = + 61.2 ° (MeOH, c = 1.00, 25 ° C).
No. 2a-78
[Α] D = + 67.4 ° (MeOH, c = 1.01, 25 ° C).
No. 2a-79
CDCl 3 300 MHz
0.99 (1H, d, J = 10.2Hz), 1.15 and 1.24 (each 3H, each s), 1.54-2.54 (14H, m), 4.31 (1H, m), 5.32-5.54 (2H, m), 6.36 (1H, d, J = 8.2 Hz), 6.93 and 7.48 (each 2H, each d, J = 8, 6 Hz), 7.59 and 7.75 (each 2H, each d, J = 8.4 Hz),
IR (CH 2 Cl 2 3 ): 3593, 3448, 3192, 3030, 3010, 2925, 2870, 1708, 1644, 1608, 1591, 1559, 1530, 1516, 1491 / cm.
[Α] D = + 65.8 ° (MeOH, c = 1.01, 25 ° C).
No. 2a-80
[Α] D = + 66.9 ° (MeOH, c = 1.01, 25 ° C).
No. 2a-81
CDCl 3 300 MHz
0.99 (1H, d, J = 10.5 Hz), 1.15 and 1.24 (each 3H, each s), 1.54-2.48 (14H, m), 3.86 (3H, s), 4.29 (1H, m), 5.34-5.52 (2H, m), 6.20 (1H, d, 8.7Hz), 6.99 and 7.55 (2H each, each d, J = 9.0 Hz), 7.61 and 7.77 (each 2H, each d, 8.7 Hz).
IR (CH 2 Cl 2 3 ): 3450, 3009, 2925, 2870, 2838, 1740, 1708, 1650, 1608, 1557, 1528, 1512, 1491 / cm.
[Α] D = + 66.2 ° (MeOH, c = 1.01, 25 ° C).
No. 2a-82
[Α] D = + 57.7 ° (MeOH, c = 1.02, 24 ° C).
No. 2a-83
CDCl 3 300 MHz
0.97 (1H, d, J = 10.2Hz), 1.12 and 1.23 (each 3H, each s), 1.54-2.48 (14H, m), 2.33 (3H , s), 4.26 (1H, m), 5.32-5.52 (2H, m), 6.25 (1H, d, 8.7Hz), 7.16 and 7.75 (2H each , each d, 8.7 Hz).
IR (CH 2 Cl 2 3 ): 3452, 3030, 3022, 3012, 2925, 2870, 1754, 1709, 1654, 1604, 1585, 1522, 1493 / cm.
[Α] D = + 57.4 ° (MeOH, c = 1.01, 24 ° C).
No. 2a-84
[Α] D = + 57.8 ° (MeOH, c = 1.01, 24 ° C).
No. 2a-85
CDCl 3 300 MHz
0.95 (1H, d, J = 10.2 Hz), 1.12 and 1.22 (each 3H, each s), 1.54-2.48 (14H, m), 4.25 (1H, m), 5.32-5.52 (2H, m), 6.28 (1H, d, 8.7 Hz), 6.87 and 7.57 (each 2H, each d, J = 9.0 Hz ).
IR (CH 2 Cl 2 3 ): 3590, 3450, 3166, 3019, 3012, 2925, 2871, 1708, 1637, 1608, 1583, 1531, 1498 / cm.
[Α] D = + 56.0 ° (MeOH, c = 1.01, 24 ° C).
No. 2a-86
[Α] D = + 59.3 ° (MeOH, c = 1.01, 22 ° C).
No. 2a-87
CDCl 3 300 MHz
0.98 (1H, d, J = 10.0 Hz), 1.13 and 1.23 (each 3H, each s), 1.54-2.48 (14H, m), 3.85 (3H, s), 4.25 (1H, m), 5.32-5.53 (2H, m), 6.19 (1H, d, J = 8.8Hz), 6.93 and 7.69 (each 2H, each d, J = 9.0 Hz).
IR (CH 2 Cl 2 3 ): 3450, 3030, 3017, 3012, 2925, 2870, 2840, 1740, 1708, 1647, 1606, 1575, 1525, 1496 / cm.
[Α] D = + 58.2 ° (MeOH, c = 0.99, 22 ° C).
No. 2a-88
[Α] D = + 50.9 ° (MeOH, c = 1.02, 25 ° C).
No. 2a-89
CDCl 3 300 MHz
0.99 (1H, d, J = 10.2Hz), 1.18 and 1.26 (each 3H, each s), 1.56-2.48 (14H, m), 4.29 (1H, m), 5.36-5.54 (2H, m), 7.03 (1H, d, 8.7 Hz), 7.21 (1H, s), 7.43 (2H, m), 7, 74 (1H, ddd, J = 1.8, 6.9 and 8.7 Hz), 8.22 (1H, dd, J = 1.8 and 8.1 Hz).
IR (CH 2 Cl 2 3 ): 3443, 3087, 3023, 3014, 2925, 2870, 1708, 1685, 1658, 1630, 1517, 1466 / cm.
[Α] D = + 57.1 ° (MeOH, c = 1.01, 22 ° C).
Mp 117.0-118.0 ° C.
No. 2a-90
[Α] D = + 54.1 ° (MeOH, c = 1.01, 22 ° C).
No. 2a-91
CDCl 3 300 MHz
0.97 (1H, d, J = 10.2 Hz), 1.13 and 1.23 (each 3H, each s), 1.52-2.46 (14H, m), 4.24 (1H, m), 5.34-5.52 (2H, m), 6.49-6.53 (12H, m), 7.11 (1H, dd, J = 0.9 and 3.6 Hz), 7 , 44 (1H, dd, J = 0.9 and 1.8 Hz).
IR (CH 2 Cl 2 3 ): 3437, 3033, 3022, 3014, 2925, 2870, 1739, 1708, 1655, 1595, 1520, 1472 / cm.
[Α] D = + 55.0 ° (MeOH, c = 1.00, 22 ° C).
No. 2a-92
[Α] D = + 50.3 ° (MeOH, c = 1.00, 22 ° C).
No. 2a-93
CDCl 3 300 MHz
0.95 (1H, d, J = 10.5 Hz), 1.12 and 1.23 (each 3H, each s), 1.52-2.46 (14H, m), 4.25 (1H, m), 5.34-5.52 (2H, m), 6.12 (1H, d, 8.7 Hz), 7.07 (1H, dd, J = 3.9 and 5.1 Hz), 7.45-7.48 (2H, m).
IR (CH 2 Cl 2 3 ): 3450, 3023, 3011, 2925, 2870, 1739, 1708, 1645, 1531, 1501, 1471 / cm.
[Α] D = + 49.1 ° (MeOH, c = 1.02, 24 ° C).
No. 2a-94
[Α] D = + 51.5 ° (MeOH, c = 1.00, 24 ° C).
No. 2a-95
CDCl 3 300 MHz
0.96 (1H, d, J = 10.5 Hz), 1.11 and 1.23 (each 3H, each s), 1.52-2.46 (14H, m), 4.25 (1H, m), 5.34-5.56 (2H, m), 6.14 (1H, d, 8.7Hz), 7.34 (2H, d, J = 2.0Hz), 7.85 ( 1H, t, J = 2.0 Hz).
IR (CH 2 Cl 2 3 ): 3452, 3114, 3030, 3013, 2925, 2870, 1708, 1649, 1535, 1498, 1471 / cm.
[Α] D = + 55.5 ° (MeOH, c = 1.00, 25 ° C).
Mp. 87.0-88.0 ° C.
No. 2a-96
CD 3 OD 300 MHz
0.94 (1H, d, J = 10.2 Hz), 1.13 and 1.22 (each 3H, each s), 1.50-1.76 (3H, m), 1.94-2, 39 (11H, m), 4.11 (1H, m), 5.39-5.49 (2H, m), 7.43-7.51 (2H, m), 8.05 (1H, m) ,
IR (KBr): 3369, 3084, 2985, 2921, 2868, 1630, 1566, 1538, 1503 / cm.
[Α] D = + 38.8 ° (MeOH, c = 1.01, 22 ° C).
No. 2a-97
CD 3 OD 300 MHz
0.93 (1H, d, J = 9.9 Hz), 1.13 and 1.22 (each 3H, each s), 1.48-1.58 (3H, m), 1.96-2, 36 (11H, m), 4.10 (1H, m), 5.35-5.50 (2H, m), 7.42-7.51 (2H, m), 8.06 (1H, m) ,
IR (KBr): 3447, 3087, 2987, 2922, 2868, 1629, 1545, 1501 / cm.
[Α] D = + 52.9 ° (MeOH, c = 1.01, 24 ° C).
No. 2a-98
[Α] D = + 53.2 ° (MeOH, c = 1.02, 23 ° C).
No. 2a-99
CDCl 3 300 MHz
0.97 (1H, d, J = 10.2 Hz), 1.12 and 1.22 (each 3H, each s), 1.26-2.45 (24H, m), 4.25 (2H, m), 5.34-5.52 (2H, m), 6.18 (1H, d, 8.7Hz), 6.91 and 7.66 (each 2H, each d, J = 9.0Hz).
IR (CH 2 Cl 2 3 ): 3455, 3029, 3019, 2939, 2862, 1738, 1709, 1645, 1605, 1523, 1494 / cm.
[Α] D = + 51.4 ° (MeOH, c = 1.00, 23 ° C).
No. 2a-100
[Α] D = + 49.3 ° (MeOH, c = 1.00, 24 ° C).
No. 2a-101
[Α] D = + 51.3 ° (MeOH, c = 1.00, 24 ° C).
No. 2a-102
[Α] D = + 48.8 ° (MeOH, c = 1.01, 23 ° C).
No. 2a-103
CDCl 3 300 MHz
0.94 (1H, d, J = 10.2 Hz), 1.12 and 1.22 (each 3H, each s), 1.52-2.46 (14H, m), 2.48 (3H, d, J = 0.3 Hz), 4.20 (1H, m), 5.32-5.54 (2H, m), 6.46 (1H, br), 7.12 (1H, d, J = 9.0 Hz).
IR (CH 2 Cl 2 3 ): 3415, 3144, 3029, 3011, 2926, 2871, 1708, 1671, 1598, 1538, 14564 / cm
[Α] D = + 49.6 ° (MeOH, c = 1.01, 23 ° C).
No. 2a-104
[Α] D = + 77.0 ° (MeOH, c = 1.02, 23 ° C).
No. 2a-105
CDCl 3 300 MHz
93 (1H, d, J = 9.9 Hz), 1.09 and 1.21 (each 3H, each s), 1.51-2.44 (14H, m), 3.90 (6H, s) , 4.20 (1H, m), 5.38-5.50 (2H, m), 5.87 (1H, d, J = 9.0 Hz), 6.25 and 7.54 (1H each, each d, J = 15.6 Hz), 6.84 (1H, d, J = 8.1 Hz), 7.03 (1H, d, J = 1.8 Hz), 7.09 (1H, dd , J = 1.8 and 8.1 Hz).
IR (CH 2 Cl 2 3 ): 3439, 3028, 3012, 2937, 2871, 2841, 1739, 1708, 1661, 1620, 1600, 1513 / cm.
[Α] D = + 77.3 ° (MeOH, c = 1.01, 23 ° C).
No. 2a-106
[Α] D = + 67.0 ° (MeOH, c = 1.00, 25 ° C).
No. 2a-107
[Α] D = + 66.6 ° (MeOH, c = 1.01, 24 ° C).
M.p. 168.0-170.0 ° C.
No. 2a-108
[Α] D = + 61.8 ° (MeOH, c = 1.00, 22 ° C).
No. 2a-109
CDCl 3 300 MHz
0.96 (1H, d, J = 10.2 Hz), 1.10 and 1.22 (each 3H, each s), 1.51-2.45 (14H, m), 4.25 (1H, m), 5.33-5.49 (2H, m), 6.21 (1H, d, 8.7 Hz), 7.25 and 7.60 (each 2H, each d, 8.7 Hz), 7.33-7.41 (5H, s).
IR (CH 2 Cl 2 3 ): 3453, 3062, 3028, 3014, 2925, 2870, 1739, 1708, 1651, 1594, 1557, 1515, 1481 / cm.
[Α] D = + 61.0 ° (MeOH, c = 1.01, 22 ° C).
No. 2a-110
CD 3 OD 300 MHz
0.94 (1H, d, J = 9.9 Hz), 1.13 and 1.22 (each 3H, each s), 1.54-2.37 (14H, m), 4.12 (1H, m), 5.38-5.49 (2H, m), 7.25 and 7.68 (each 2H, each d, 8.7 Hz), 7.41 (5H, s).
IR (KBr): 3435, 3058, 2986, 2920, 2866, 1635, 1595, 1562, 1521, 1482, 1439, 1411 / cm.
[Α] D = + 47.3 ° (MeOH, c = 1.01, 23 ° C).
No. 2a-111
[Α] D = + 65.6 ° (MeOH, c = 1.01, 24 ° C).
No. 2a-112
CDCl 3 300 MHz
0.97 (1H, d, J = 10.2Hz), 1.12 and 1.23 (each 3H, each s), 1.51-2.46 (14H, m), 4.27 (1H, m), 5.35-5.50 (2H, m), 6.22 (1H, d, J = 8.4 Hz), 7.40 and 7.66 (each 2H, each d, J = 9, 0 Hz).
IR (CH 2 Cl 2 3 ): 3439, 3028, 3012, 2937, 2871, 2841, 1739, 1708, 1661, 1620, 1600, 1513 / cm.
[Α] D = + 65.6 ° (MeOH, c = 1.01, 22 ° C).
No. 2a-113
[Α] D = + 59.6 ° (MeOH, c = 1.00, 24 ° C).
No. 2a-114
CDCl 3 300 MHz
0.98 (1H, d, J = 10.2Hz), 1.12 and 1.24 (each 3H, each s), 1.52-2.46 (14H, m), 4.29 (1H, m), 5.35-5.51 (2H, m), 6.28 (1H, d, J = 8.4 Hz), 7.70 and 7.83 (each 2H, each d, J = 8, 4 Hz).
IR (CH 2 Cl 2 3 ): 3439, 3028, 3012, 2937, 2871, 2841, 1739, 1708, 1661, 1620, 1600, 1513 / cm.
[Α] D = + 60.6 ° (MeOH, c = 1.01, 22 ° C).
No. 2a-115
[Α] D = + 59.7 ° (MeOH, c = 0.99, 24 ° C).
No. 2a-116
CDCl 3 300 MHz
0.97 (1H, d, J = 10.2 Hz), 1.12 and 1.23 (each 3H, each s), 1.52-2.46 (14H, m), 2.39 (3H, s), 4.27 (1H, m), 5.33-5.51 (2H, m), 6.24 (1H, d, J = 9.0 Hz), 7.23 and 7.62 (each 2H, each d, J = 8.4 Hz).
IR (CH 2 Cl 2 3 ): 3439, 3028, 3012, 2937, 2871, 2841, 1739, 1708, 1661, 1620, 1600, 1513 / cm.
[Α] D = + 59.7 ° (MeOH, c = 0.99, 24 ° C).
No. 2a-117
[Α] D = + 56.7 ° (MeOH, c = 1.00, 23 ° C).
No. 2a-118
CDCl 3 300 MHz
0.96 (1H, d, J = 10.2 Hz), 1.11 and 1.23 (each 3H, each s), 1.53-2.44 (14H, m), 4.23 (1H, m), 5.34-5.51 (2H, m), 6.02 (2H, s), 6.13 (1H, d, J = 8.7Hz), 6.83 (1H, dd, J = 1.2 and 7.8 Hz), 7.22-7.25 (2H, m).
IR (CH 2 Cl 2 3 ): 3453, 3031, 3020, 3012, 2924, 2870, 1740, 1708, 1650, 1619, 1605, 1519, 1504, 1480 / cm.
[Α] D = + 57.2 ° (MeOH, c = 1.02, 23 ° C).
No. 2a-119
CDCl 3 300 MHz
0.96 (1H, d, J = 10.5 Hz), 1.07 and 1.23 (each 3H, each s), 1.51-2.44 (14H, m), 2.32 (3H, s), 4.26 (1H, m), 5.37-5.52 (2H, m), 6.40 (1H, d, J = 9.0 Hz), 7.09 (1H, m), 7.30 (1H, m), 7.46 (1H, m), 7.66 (1H, m).
IR (CH 2 Cl 2 3 ): 3443, 3028, 3012, 2925, 2870, 1766, 1747, 1709, 1657, 1607, 1516, 1479 / cm.
[Α] D = + 53.2 ° (MeOH, c = 0.99, 21 ° C).
No. 2a-120
CDCl 3 300 MHz
0.98 (1H, d, J = 10.2Hz), 1.14 and 1.24 (each 3H, each s), 1.53-2.44 (14H, m), 4.30 (1H, m), 5.35-5.52 (2H, m), 6.42 (1H, d, 8.7Hz), 6.85 (1H, m), 6.99 (1H, dd, J = 1 , 2 and 8.4 Hz), 7.27 (1H, m), 7.39 (1H, m).
IR (CH 2 Cl 2 3 ): 3463, 3033, 3021, 3014, 2992, 2924, 2870, 1708, 1643, 1597, 1523, 1488 / cm.
[Α] D = + 46.3 ° (MeOH, c = 1.01, 21 ° C).
No. 2a-121
CDCl 3 300 MHz
0.98 (1H, d, J = 10.2Hz), 1.14 and 1.23 (each 3H, each s), 1.47-2.47 (14H, m), 3.95 (3H, s), 4.31 (1H, m), 5.32-5.50 (2H, m), 6.98 (1H, dd, J = 0.9 and 8.4 Hz), 7.09 (1H , ddd, J = 0.9, 7.7 and 8.4 Hz), 7.45 (1H, m), 8.19 (1H, dd, J = 2.1 and 8.1 Hz), 8, 32 (1H, d, J = 9.0 Hz).
IR (CH 2 Cl 2 3 ): 3400, 3078, 3028, 3020, 3007, 2924, 2870, 2842, 1736, 1708, 1640, 1600, 1536, 1483, 1470 / cm.
[Α] D = + 38.1 ° (MeOH, c = 1.02, 23 ° C).
No. 2a-122
[Α] D = + 42.3 ° (MeOH, c = 0.99, 23 ° C).
No. 2a-123
[Α] D = + 38.7 ° (MeOH, c = 1.00, 21 ° C).
No. 2a-124
[Α] D = + 45.0 ° (MeOH, c = 1.01, 21 ° C).
Mp 119.0-120.0 ° C.
No. 2a-125
[Α] D = + 49.8 ° (MeOH, c = 1.01, 22 ° C).
No. 2a-126
CDCl 3 300 MHz
0.97 (1H, d, J = 10.2 Hz), 1.11 and 1.23 (each 3H, each s), 1.52-2.47 (14H, m), 4.26 (1H, m), 5.34-5.50 (2H, m), 6.22 (1H, d, 8.7Hz), 7.55-7.61 (4H, m).
IR (CH 2 Cl 2 3 ): 3400, 3078, 3028, 3020, 3007, 2924, 2870, 2842, 1736, 1708, 1640, 1600, 1536, 1483, 1470 / cm.
[Α] D = + 63.0 ° (MeOH, c = 1.01, 23 ° C).
No. 2a-127
CDCl 3 300 MHz
0.91 (1H, d, J = 10.2 Hz), 1.10 and 1.20 (each 3H, each s), 1.50-2.42 (14H, m), 4.23 (1H, m), 5.31-5.51 (2H, m), 6.45 (1H, d, J = 8.4 Hz), 7.01 (1H, t, J = 7.4 Hz), 7, 22-7.27 (2H, m), 7.33-7.40 (4H, m), 7.53 (2H, d, J = 9.0, Hz), 8.30 and 8.48 (each 1H, each s).
IR (CH 2 Cl 2 3 ): 3452, 3028, 3022, 3015, 2925, 2870, 1708, 1654, 1590, 1514, 1478 / cm.
[Α] D = + 59.5 ° (MeOH, c = 1.01, 23 ° C).
No. 2a-128
d 6 -DMSO 300 MHz
0.84 (1H, d, J = 9.9Hz), 1.06 and 1.19 (each 3H, each s), 1.37-2.37 (14H, m), 3.79 (1H, m), 5.35-5.51 (2H, m), 6.08 (1H, d, 8.7Hz), 6.85-6.90 (1H, m), 7.18-7.23 (2H, m), 7.35-7.38 (2H, m), 8.42 (1H, s), 12.00 (1H, s).
IR (Nujol): 3395, 3345, 2925, 2866, 2623, 2506, 1697, 1658, 1638, 1597, 1557 / cm.
[Α] D = + 26.0 ° (MeOH, c = 1.01, 23 ° C).
Mp 164.0-166.0 ° C.
No. 2a-129
CDCl 3 300 MHz
1.01 (1H, d, J = 10.0 Hz), 1.17 and 1.25 (each 3H, each s), 1.54-2.52 (14H, m), 4.34 (1H, m), 5.36-5.57 (2H, m), 6.42 (1H, d, J = 8.6Hz), 7.51-7.60 (2H, m), 7.77 (1H , dd, J = 1.8 and 8.6 Hz), 7.85-7.96 (3H, m), 8.24 (1H, br).
IR (CH 2 Cl 2 3 ): 3451, 3060, 3028, 3010, 2925, 2870, 1708, 1652, 1629, 1600, 1517, 1502 / cm.
[Α] D = + 68.6 ° (MeOH, c = 1.00, 22 ° C).
No. 2a-130
CDCl 3 300 MHz
1.02 (1H, d, J = 10.2 Hz), 1.04 and 1.26 (each 3H, each s), 1.54-2.52 (14H, m), 4.41 (1H, m), 5.41-5.58 (2H, m), 6.14 (1H, d, J = 9.0 Hz), 7.43-7.59 (4H, m), 7.85-7 , 92 (2H, m), 8.27 (1H, dd, J = 1.8 and 7.2 Hz).
IR (CH 2 Cl 2 3 ): 3436, 3032, 3010, 2924, 2870, 2664, 1708, 1652, 1512, 1498 / cm.
[Α] D = + 93.9 ° (MeOH, c = 1.00, 22 ° C).
Mp. 94.0-96.0 ° C.
No. 2a-131
[Α] D = + 50.2 ° (MeOH, c = 0.95, 21 ° C).
No. 2a-132
[Α] D = + 10.9 ° (MeOH, c = 0.92, 21 ° C).
No. 2a-133
[Α] D = + 60.4 ° (MeOH, c = 1.00, 21 ° C).
No. 2a-134
[Α] D = + 38.5 ° (MeOH, c = 1.01, 23 ° C).
No. 2a-135
[Α] D = + 52.5 ° (MeOH, c = 1.01, 23 ° C).
Mp. 180.0-182.0 ° C.
No. 2a-136
[Α] D = + 35.3 ° (MeOH, c = 1.02, 23 ° C).
M.p. 79.0-80.0 ° C.
No. 2a-137
CDCl 3 300 MHz
0.97 (1H, d, J = 10.2Hz), 1.11 and 1.22 (each 3H, each s), 1.43 (3H, t, J = 6.9Hz), 1.52 -2.44 (14H, m), 4.03 (2H, q, J = 6.9 Hz), 4.26 (1H, m), 5.33-5.50 (2H, m), 6, 19 (1H, d, 8.7Hz), 6.88-7.00 (6H, m), 7.65-7.68 (2H, m).
IR (CH 2 Cl 2 3 ): 3455, 3031, 3024, 3014, 2988, 2925, 2870, 1741, 1708, 1649, 1602, 1521, 1504, 1490 / cm.
[Α] D = + 52.0 ° (MeOH, c = 1.01, 23 ° C).
No. 2a-138
CDCl 3 300 MHz
0.97 (1H, d, J = 10.2Hz), 1.11 and 1.22 (each 3H, each s), 1.35 (6H, d, J = 6.0Hz), 1.53 -2,46 (14H, m), 4,25 (1H, m), 4,51 (1H, m), 5,33-5,50 (2H, m), 6,12 (1H, d, J = 9.0 Hz), 6.87-6.99 (6H, m), 7.65-7.68 (2H, m).
IR (CH 2 Cl 2 3 ): 3454, 3031, 3014, 2980, 2925, 2870, 1741, 1708, 1649, 1602, 1522, 1490 / cm.
[Α] D = + 50.0 ° (MeOH, c = 1.05, 22 ° C).
No. 2a-139
CDCl 3 300 MHz
1.00 (1H, d, J = 10.2Hz), 1.16 and 1.24 (each 3H, each s), 1.59-2.52 (14H, m), 4.31 (1H, m), 5.40-5.53 (2H, m), 6.36 (1H, d, 8.7Hz), 6.70 (1H, d, J = 1.5Hz), 7.12 ( 1H, m), 7.30 (1H, m), 7.47 (1H, dd, J = 0.6 and 8.1 Hz), 7.61 (1H, d, J = 8.4 Hz).
IR (CH 2 Cl 2 3 ): 3449, 3243, 3029, 3022, 3013, 2925, 2871, 1707, 1631, 1542, 1505 / cm.
[Α] D = + 63.4 ° (MeOH, c = 1.00, 23 ° C).
M.p. 178.0-179.0 ° C.
No. 2a-140
CDCl 3 300 MHz
0.97 (1H, d, J = 10.2Hz), 1.18 and 1.23 (each 3H, each s), 1.57-2.50 (14H, m), 4.35 (1H, m), 5.32-5.55 (2H, m), 6.42 (1H, d, 8.7 Hz), 6.70 (1H, d, J = 1.5 Hz), 7.21 7.24 (2H, m), 7.46 (1H, m), 7.76 (1H, m), 7.86 (1H, d, J = 3.0 Hz), 10.20 (1H, s ).
IR (CH 2 Cl 2 3 ): 3465, 3010, 2924, 1739, 1604, 1546, 1504 / cm.
[Α] D = + 39.4 ° (MeOH, c = 1.01, 22 ° C).
Mp 167.0-168.0 ° C.
No. 2a-141
CDCl 3 300 MHz
0.99 (1H, d, J = 10.2Hz), 1.14 and 1.24 (each 3H, each s), 1.55-2.44 (14H, m), 3.84 (3H, s), 4.27 (1H, m), 5.34-5.52 (2H, m), 6.28 (1H, d, J = 9.0 Hz), 6.91 and 7.47 (each 2H, each d, J = 9.0 Hz), 6.98 and 7.14 (each 1H, each d, J = 16.5 Hz), 7.54 and 7.70 (each 2H, each d, 8) , 7 Hz).
IR (CH 2 Cl 2 3 ): 3453, 3025, 3015, 2925, 2870, 2839, 1740, 1708, 1649, 1602, 1510, 1493, 1470 / cm.
[Α] D = + 73.4 ° (MeOH, c = 1.02, 22 ° C).
Mp. 155.0-157.0 ° C.
No. 2a-142
CDCl 3 300 MHz
0.97 (1H, d, J = 10.2 Hz), 1.11 and 1.23 (each 3H, each s), 1.52-2.45 (14H, m), 3.79 (3H, s), 4.27 (1H, m), 5.34-5.50 (2H, m), 6.24 (1H, d, J = 9.0 Hz), 6.49 and 6.62 (each 1H, each d, J = 12.3 Hz), 6.77 and 7.16 (each 2H, each d, 8.7 Hz), 7.32 and 7.59 (each 2H, each d, J = 8) , 1 Hz).
IR (CH 2 Cl 2 3 ): 3453, 3025, 3014, 2925, 2870, 2839, 1739, 1708, 1649, 1606, 1510, 1494 / cm.
[Α] D = + 60.7 ° (MeOH, c = 0.99, 22 ° C).
No. 2a-143
[Α] D = + 57.3 ° (MeOH, c = 1.01, 23 ° C).
No. 2a-144
[Α] D = + 12.2 ° (MeOH, c = 1.00, 23 ° C).
Mp. 114.0-116.0 ° C.
No. 2a-145
CDCl 3 300 MHz
0.95 (1H, d, J = 10.2Hz), 1.10 and 1.21 (each 3H, each s), 1.52-2.44 (14H, m), 4.25 (1H, m), 5.33-5.49 (2H, m), 6.37 (1H, d, 8.7Hz), 7.45-7.47 (3H, m), 7.62-7.66 (2H, m), 7.69 and 7.80 (each 2H, each d, J = 7.5 Hz).
IR (CH 2 Cl 2 3 ): 3449, 3058, 3027, 3012, 2925, 2870, 1708, 1655, 1513, 1481, 1043 / cm.
[Α] D = + 61.0 ° (MeOH, c = 1.01, 23 ° C).
No. 2a-146
CDCl 3 300 MHz
0.95 (1H, d, J = 10.5 Hz), 1.09 and 1.21 (each 3H, each s), 1.50-2.41 (14H, m), 4.25 (1H, m), 5.33-5.49 (2H, m), 6.33 (1H, d, J = 8.4Hz), 7.49-7.61 (3H, m), 7.91-7 , 92 (2H, m), 7.82 and 7.97 (each 2H, each d, 8.7 Hz).
IR (CH 2 Cl 2 3 ): 3447, 3029, 3023, 3015, 2925, 2870, 1708, 1660, 1514, 1484, 1321, 1161 / cm.
[Α] D = + 62.0 ° (MeOH, c = 1.00, 22 ° C).
No. 2a-147
CDCl 3 300 MHz
0.97 (1H, d, J = 10.2 Hz), 1.12 and 1.23 (each 3H, each s), 1.52-2.46 (14H, m), 2.51 (3H, s), 4.26 (1H, m), 5.34-5.51 (2H, m), 6.23 (1H, d, J = 8.4Hz), 7.26 and 7.64 (each 2H, each d, J = 8.4 Hz).
IR (CH 2 Cl 2 3 ): 3453, 3027, 3015, 2925, 2870, 2665, 1708, 1648, 1596, 1516, 1484 / cm.
[Α] D = + 67.7 ° (MeOH, c = 0.82, 22 ° C).
No. 2a-148
[Α] D = + 72.5 ° (MeOH, c = 1.01, 25 ° C).
No. 2a-149
[Α] D = + 67.8 ° (MeOH, c = 0.98, 25 ° C).
No. 2a-150
CDCl 3 300 MHz
0.94 (1H, d, J = 10.2 Hz), 1.10 and 1.23 (each 3H, each s), 1.52-2.50 (14H, m), 4.22 (1H, m), 5.36-5.55 (2H, m), 6.48 (1H, d, J = 8.4Hz), 8.35 (1H, s), 8.90 (1H, s).
IR (CH 2 Cl 2 3 ): 3443, 3374, 3091, 3024, 3012, 2925, 2871, 1709, 1652, 1525, 1494 / cm.
[Α] D = + 58.1 ° (MeOH, c = 1.01, 23 ° C).
Mp 120,0-122,0 ° C.
No. 2a-151
[Α] D = + 40.6 ° (MeOH, c = 1.01, 23 ° C).
No. 2a-152
CDCl 3 300 MHz
0.96 (1H, d, J = 10.5 Hz), 1.10 and 1.24 (each 3H, each s), 1.50-2.50 (14H, m), 2.71 (3H, s), 4.26 (1H, m), 5.37-5.51 (2H, m), 6.02 (1H, d, J = 9.0 Hz), 8.73 (1H, s).
IR (CH 2 Cl 2 3 ): 3463, 3435, 3087, 3025, 3014, 2925, 2870, 1708, 1649, 1523, 1503 / cm.
[Α] D = + 54.1 ° (MeOH, c = 1.02, 22 ° C).
No. 2a-153
CDCl 3 300 MHz
0.95 (1H, d, J = 9.9 Hz), 1.11 and 1.23 (each 3H, each s), 1.50-2.50 (14H, m), 2.50 (3H, s), 4.26 (1H, m), 5.36-5.51 (2H, m), 6.01 (1H, d, J = 8.4Hz), 6.88 (1H, d, J = 5.1 Hz), 7.26 (1H, d, J = 5.1 Hz).
IR (CH 2 Cl 2 3 ): 3469, 3431, 3025, 3013, 2925, 2871, 2664, 1708, 1639, 1544, 1505 / cm.
[Α] D = + 35.8 ° (MeOH, c = 1.03, 22 ° C).
No. 2a-154
CDCl 3 300 MHz
0.95 (1H, d, J = 9.9 Hz), 1.10 and 1.22 (each 3H, each s), 1.52-2.46 (14H, m), 2.51 (3H, d, J = 1.2 Hz), 4.26 (1H, m), 5.34-5.50 (2H, m), 6.00 (1H, d, J = 8.4 Hz), 6, 73 (1H, dd, J = 5.1 and 3.6 Hz), 7.29 (1H, d, J = 3.6 Hz).
IR (CH 2 Cl 2 3 ): 3450, 3431, 3026, 3011, 2925, 2869, 1739, 1708, 1639, 1547, 1508 / cm.
[Α] D = + 50.5 ° (MeOH, c = 1.01, 22 ° C).
No. 2a-155
CDCl 3 300 MHz
0.99 (1H, d, J = 10.2Hz), 1.19 and 1.25 (each 3H, each s), 1.53-2.48 (14H, m), 4.31 (1H, m), 5.36-5.51 (2H, m), 6.79 (1H, d, J = 9.3Hz), 7.29 (1H, m), 7.41 (1H, m), 7.48 (1H, s), 7.51 (1H, m), 7.66 (1H, d, J = 8.1 Hz).
IR (CH 2 Cl 2 3 ): 3436, 3029, 3024, 3015, 2925, 2871, 2670, 1708, 1659, 1598, 1510 / cm.
[Α] D = + 69.1 ° (MeOH, c = 1.01, 22 ° C).
No. 2a-156
CDCl 3 :CD 3 OD = 10: 1, 300 MHz
0.99 (1H, d, J = 9.9 Hz), 1.11 and 1.21 (each 3H, each s), 1.56-2.58 (14H, m), 4.22 (1H, m), 5.35-5.59 (2H, m), 6.83 (1H, d, J = 8.4Hz), 7.48 (1H, d, J = 8.4Hz), 7, 61 (1H, dd, J = 1.5 and 8.4 Hz), 8.09 (1H, d, J = 1.5 Hz), 8.12 (1H, s).
IR (KBr): 3422, 3115, 2985, 2922, 2869, 2609, 1708, 1636, 1578, 1529, 1470 / cm.
[Α] D = + 62.8 ° (MeOH, c = 1.01, 22 ° C).
No. 2a-157
[Α] D = + 40.0 ° (MeOH, c = 0.95, 22 ° C).
No. 2a-158
CDCl 3 300 MHz
1.00 (1H, d, J = 10.5 Hz), 1.17 and 1.24 (each 3H, each s), 1.54-2.50 (14H, m), 4.34 (1H, m), 5.36-5.52 (2H, m), 7.80 (1H, d, J = 9.0 Hz), 9.30 (1H, s).
IR (CH 2 Cl 2 3 ): 3410, 3122, 3030, 3012, 2925, 2871, 2668, 1709, 1667, 1538, 1466 / cm.
[Α] D = + 44.9 ° (MeOH, c = 0.99, 22 ° C).
No. 2a-159
CDCl 3 300 MHz
0.97 (1H, d, J = 10.2Hz), 1.13 and 1.22 (each 3H, each s), 1.55-2.43 (14H, m), 3.03 (6H, s), 4.23 (1H, m), 5.32-5.51 (2H, m), 6.16 (1H, d, 8.7Hz), 6.87 and 7.63 (2H each, each d, 8.7 Hz).
IR (CH 2 Cl 2 3 ): 3457, 3028, 3006, 2924, 2870, 2654, 1739, 1709, 1637, 1608, 1608, 1534, 1501 / cm.
[Α] D = + 64.8 ° (MeOH, c = 1.01, 22 ° C).
No. 2a-160
d 6 -DMSO 300 MHz
0.83 (1H, d, J = 9.9 Hz), 1.02 and 1.19 (each 3H, each s), 1.38-1.61 (3H, m), 1.90-2, 32 (11H, m), 3.90 (1H, m), 5.41-5.44 (2H, m), 7.32 (1H, dd, J = 0.9 and 7.2 Hz), 7 , 45-7.60 (2H, m), 7.77 (1H, dd, J = 0.9 and 7.8 Hz), 8.03 (1H, d, J = 6.9 Hz), 12, 40 (1H, s).
IR (Nujol): 3315, 2924, 2856, 2656, 2535, 1737, 1703, 1637, 1598, 1581, 1541 / cm.
[Α] D = + 78.5 ° (MeOH, c = 1.01, 24 ° C).
M.p. 161.0-162.0 ° C.
No. 2a-161
[Α] D = + 65.3 ° (MeOH, c = 1.00, 22 ° C).
No. 2a-162
CDCl 3 300 MHz
0.99 (1H, d, J = 10.2 Hz), 1.13 and 1.25 (each 3H, each s), 1.53-2.45 (14H, m), 4.30 (1H, m), 5.36-5.51 (2H, m), 6.32 (1H, d, J = 8.4Hz), 7.88 and 8.28 (each 2H, each d, J = 9, 0 Hz).
IR (CH 2 Cl 2 3 ): 3448, 3029, 3016, 2925, 2870, 1708, 1664, 1602, 1527, 1484, 1347 / cm.
[Α] D = + 72.7 ° (MeOH, c = 1.02, 22 ° C).
No. 2a-163
CDCl 3 300 MHz.
0.96 (1H, d, J = 10.2Hz), 1.11 and 1.23 (each 3H, each s), 1.55-2.51 (14H, m), 4.26 (1H, m), 5.36-5.57 (2H, m), 6.68 (1H, d, J = 7.8 Hz), 7.41 (1H, dd, J = 4.8 and 8.1 Hz ), 8.20 (1H, d, J = 8.1 Hz), 8.66 (1H, d, J = 4.8 Hz), 9.00 (1H, s).
IR (CH 2 Cl 2 3 ): 3448, 3026, 3013, 2925, 2870, 2534, 1709, 1658, 1590, 1515, 1471 / cm.
[Α] D = + 71.3 ° (MeOH, c = 1.01, 22 ° C).
No. 2a-164
[Α] D = + 40.8 ° (MeOH, c = 0.98, 22 ° C).
No. 2a-165
CDCl 3 300 MHz
0.96 (1H, d, J = 10.5 Hz), 1.11 and 1.24 (each 3H, each s), 1.55-2.52 (14H, m), 4.24 (1H, m), 5.37-5.57 (2H, m), 6.63 (1H, d, J = 7.8Hz), 7.59 and 8.63 (each 2H, each d, J = 6, 0 Hz).
IR (CH 2 Cl 2 3 ): 3447, 3346, 3028, 3016, 2925, 2870, 2538, 1941, 1708, 1662, 1556, 1516 / cm.
[Α] D = + 75.4 ° (MeOH, c = 1.01, 22 ° c).
No. 2a-166
CDCl 3 300 MHz
0.97 (1H, d, J = 10.2Hz), 1.11 and 1.22 (each 3H, each s), 1.51-2.44 (14H, m), 2.95 (6H, s), 4.25 (1H, m), 5.33-5.50 (2H, m), 6.19 (1H, d, 8.7Hz), 6.77 and 6.97 (2H each, each d, J = 8.4 Hz), 6.94 and 7.65 (each 2H, each d, J = 9.0 Hz).
IR (CH 2 Cl 2 3 ): 3453, 3024, 3016, 2924, 2871, 2806, 1739, 1708, 1647, 1612, 1604, 1515, 1490 / cm.
[Α] D = + 53.1 ° (MeOH, c = 1.02, 23 ° C).
M.p. 104.0-105.5 ° C.
No. 2a-167
CDCl 3 300 MHz
1.01 (1H, d, J = 9.9 Hz), 1.19 and 1.26 (each 3H, each s), 1.56-2.53 (14H, m), 4.37 (1H, m), 5.35-5.55 (2H, m), 6.47 (1H, d, J = 8.4Hz), 7.61-7.71 (2H, m), 7.79 (2H , s), 7.89-7.97 (2H, m), 8.27 (1H, d, J = 2, 1 Hz), 8.66-8.73 (2H, m).
IR (CH 2 Cl 2 3 ): 3450, 3024, 3014, 2925, 2870, 2667, 1707, 1650, 1531, 1509 / cm.
[Α] D = + 70.5 ° (MeOH, c = 1.00, 22 ° C).
No. 2a-168
CDCl 3 300 MHz
1.02 (1H, d, J = 10.2 Hz), 1.20 and 1.26 (each 3H, each s), 1.56-2.50 (14H, m), 4.38 (1H, m), 5.36-5.56 (2H, m), 6.51 (1H, d, J = 8.4Hz), 7.61-7.93 (7H, m), 8.74 (1H , d, J = 8.4 Hz), 9.15 (1H, s).
IR (CH 2 Cl 2 3 ): 3517, 3451, 3060, 3028, 3011, 2925, 2870, 2664, 1709, 1651, 1519, 1498 / cm.
[Α] D = + 54.4 ° (MeOH, c = 1.00, 23 ° C).
No. 2a-169
CDCl 3 300 MHz
0.96 (1H, d, J = 10.5 Hz), 1.09 and 1.21 (each 3H, each s), 1.50-2.44 (14H, m), 3.85 (3H, s), 4.24 (1H, m), 5.32-5.48 (2H, m), 6.19 (1H, d, J = 8.4Hz), 6.94 and 7.45 (each 2H, each d, J = 9.0 Hz), 7.11 and 7.45 (each 2H, each d, 8.7 Hz).
IR (CH 2 Cl 2 3 ): 3516, 3453, 3029, 3009, 2925, 2870, 2840, 2665, 1708, 1650, 1593, 1515, 1493, 1482 / cm.
[Α] D = + 57.8 ° (MeOH, c = 1.00, 23 ° C).
No. 2a-170
CDCl 3 300 MHz
0.98 (1H, d, J = 10.2Hz), 1.15 and 1.24 (each 3H, each s), 1.52-2.50 (14H, m), 4.28 (1H, m), 5.33-5.54 (2H, m), 6.25 (1H, d, J = 8.2Hz), 7.38-7.44 (2H, m), 7.74 (1H , s), 7.81-7.86 (2H, m).
IR (CH 2 Cl 2 3 ): 3517, 3448, 3427, 3024, 3013, 2925, 2870, 2669, 1708, 1650, 1562, 1535, 1500 / cm.
[Α] D = + 61.6 ° (MeOH, c = 1.00, 23 ° C).
No. 2a-171
CDCl 3 300 MHz
0.96 (1H, d, J = 10.2 Hz, 1.11 and 1.22 (each 3H, each s), 1.52-2.42 (14H, m), 2.48 (3H, s ), 4.21 (1H, m), 5.31-5.52 (2H, m), 6.06 (1H, d, J = 8.2Hz), 6.97 and 7.59 (each 1H , each d, J = 1.2 Hz).
IR (CH 2 Cl 2 3 ): 3452, 3113, 3028, 3007, 2925, 2870, 2669, 1708, 1645, 1554, 1509 / cm.
[Α] D = + 52.4 ° (MeOH, c = 1.00, 23 ° C).
No. 2a-172
CDCl 3 300 MHz
0.96 (1H, d, J = 10.2 Hz), 1.09 and 1.28 (each 3H, each s), 1.50-2.40 (14H, m), 2.69 (3H, s), 4.24 (1H, m), 5.35-5.51 (2H, m), 5.96 (1H, d, 8.7Hz), 7.03 and 7.07 (each 1H, each d, J = 5.4 Hz).
IR (CH 2 Cl 2 3 ): 3451, 3031, 3013, 2925, 2870, 2666, 1708, 1647, 1542, 1497 / cm.
[Α] D = + 51.2 ° (MeOH, c = 1.00, 23 ° C).
No. 2a-173
CDCl 3 300 MHz
0.95 (1H, d, J = 10.2Hz), 1.10 and 1.23 (each 3H, each s), 1.50-2.45 (14H, m), 4.22 (1H, m), 5.35-5.49 (2H, m), 6.05 (1H, d, J = 8.4 Hz), 7.26
and 7.75 (each 1H, each d, J = 1.5 Hz).
IR (CH 2 Cl 2 3 ): 3451, 3011, 3029, 3011, 2925, 2870, 1708, 1652, 1538, 1500 / cm.
[Α] D = + 50.6 ° (MeOH, c = 1.01, 23 ° C).
No. 2a-174
CDCl 3 300 MHz
0.96 (1H, d, J = 10.2 Hz), 1.13 and 1.23 (each 3H, each s), 1.52-2.50 (14H, m), 4.29 (1H, m), 5.35-5.51 (2H, m), 7.02 (1H, d, J = 8.4Hz), 7.32 and 8.16 (each 1H, each d, J = 3, 9 Hz).
IR (CH 2 Cl 2 3 ): 3417, 3115, 3023, 3014, 2925, 2870, 1708, 1645, 1530 / cm.
[Α] D = + 48.8 ° (MeOH, c = 1.02, 23 ° C).
No. 2a-175
CDCl 3 300 MHz
0.97 (1H, d, J = 10.2Hz), 1.14 and 1.23 (each 3H, each s), 1.50-2.52 (14H, m), 2.52 (3H, s), 4.29 (1H, m), 5.34-5.51 (2H, m), 7.78 (1H, d, J = 9.0 Hz), 7.24 and 7.52 (each 1H, each d, J = 5.4 Hz).
IR (CH 2 Cl 2 3 ): 3329, 3093, 3023, 3015, 2924, 2871, 1708, 1640, 1526 / cm.
[Α] D = + 45.0 ° (MeOH, c = 1.01, 23 ° C).
No. 2a-176
CDCl 3 300 MHz
0.95 (1H, d, J = 10.5 Hz), 1.09 and 1.23 (each 3H, each s), 1.52-2.46 (14H, m), 2.40 (3H, d, J = 0.9 Hz), 4.24 (1H, m), 5.35-5.51 (2H, m), 6.05 (1H, d, 8.7 Hz), 6.95 ( 1H, m), 7.57 (1H, d, J = 3.3 Hz).
IR (CH 2 Cl 2 3 ): 3517, 3444, 3103, 3024, 3013, 2926, 2870, 1739, 1748, 1649, 1636, 1507 / cm.
[Α] D = + 54.8 ° (MeOH, c = 1.01, 23 ° C).
M.p. 97.0-99.0 ° C.
No. 2a-177
CDCl 3 300 MHz
0.97 (1H, d, J = 10.2 Hz), 1.11 and 1.23 (each 3H, each s), 1.52-2.45 (14H, m), 3.93 (3H, s), 4.27 (1H, m), 5.34-5.50 (2H, m), 6.35 (1H, d, J = 3.3Hz), 7.80 (1H, d, 8 , 7 Hz), 8.10 (1H, d, J = 3.3 Hz).
IR (CH 2 Cl 2 3 ): 3395, 3121, 3031, 3019, 3012, 2925, 2871, 1739, 1709, 1640, 1557, 1533 / cm.
[Α] D = + 22.8 ° (MeOH, c = 1.01, 23 ° C).
M.p. 109.0-112.0 ° C.
No. 2a-178
CDCl 3 300 MHz
0.96 (1H, d, J = 10.5 Hz), 1.10 and 1.23 (each 3H, each s), 1.51-2.45 (14H, m), 4.24 (1H, m), 5.35-5.50 (2H, m), 6.09 (1H, d, J = 8.4Hz), 7.17-7.31 (6H, m), 7.95 (1H , d, J = 1.5 Hz).
IR (CH 2 Cl 2 3 ): 3510, 3451, 3062, 3031, 3022, 3011, 2925, 2870, 2662, 1708, 1651, 1582, 1535, 1497, 1477 / cm.
[Α] D = + 47.9 ° (MeOH, c = 1.01, 25 ° C).
No. 2a-179
CDCl 3 300 MHz
0.96 (1H, d, J = 10.2Hz), 1.14 and 1.24 (each 3H, each s), 1.52-2.48 (14H, m), 4.30 (1H, m), 5.36-5.52 (2H, m), 6.73 (1H, d, J = 9.0 Hz), 6.26 and 7.37 (each 1H, each d, J = 6, 0 Hz).
IR (CH 2 Cl 2 3 ): 3509, 3429, 3115, 3094, 3025, 3014, 2925, 2871, 2666, 1708, 1649, 1529, 1510 / cm.
[Α] D = + 51.0 ° (MeOH, c = 1.02, 25 ° C).
No. 2a-180
CDCl 3 300 MHz
0.95 (1H, d, J = 10.2Hz), 1.14 and 1.24 (each 3H, each s), 1.52-2.46 (14H, m), 3.89 (3H, s), 4.21 (1H, m), 5.35-5.50 (2H, m), 6.05 (1H, d, J = 8.4Hz), 6.46 and 7.04 (each 1H, each d, J = 1.8 Hz).
IR (CH 2 Cl 2 3 ): 3516, 3450, 3114, 3031, 3010, 2925, 2871, 1708, 1648, 1546, 1511, 1477 / cm.
[Α] D = + 49.1 ° (MeOH, c = 1.01, 25 ° C).
No. 2a-181
CDCl 3 300 MHz
0.97 (1H, d, J = 10.2 Hz), 1.14 and 1.23 (each 3H, each s), 1.52-2.48 (14H, m), 2.42 (3H, s), 4.31 (1H, m), 5.34-5.52 (2H, m), 8.07 (1H, d, J = 9.3Hz), 7.27 and 8.17 (each 1H, each d, J = 3.3 Hz).
IR (CH 2 Cl 2 3 ): 3510, 3301, 3112, 3023, 3007, 2924, 2871, 2663, 1708, 1636, 1534 / cm.
[Α] D = + 41.0 ° (MeOH, c = 0.96, 25 ° C).
No. 2a-182
CDCl 3 300 MHz
0.96 (1H, d, J = 10.2 Hz), 1.11 and 1.23 (each 3H, each s), 1.53-2.46 (14H, m), 2.51 (3H, s), 4.21 (1H, m), 5.35-5.51 (2H, m), 6.05 (1H, d, J = 8.1Hz), 7.26 and 7.78 (each 1H, each d, J = 1.8 Hz).
IR (CH 2 Cl 2 3 ): 3509, 3450, 3109, 3024, 3012, 2925, 2870, 2666, 1708, 1650, 1535, 1498, 1471 / cm.
[Α] D = + 52.9 ° (MeOH, c = 0.95, 25 ° C).
No. 2a-183
CDCl 3 300 MHz
0.96 (1H, d, J = 10.5 Hz), 1.12 and 1.22 (each 3H, each s), 1.52-2.46 (14H, m), 4.25 (1H, m), 5.33-5.51 (2H, m), 6.17 (1H, d, 8.7Hz), 7.01-7.05 (3H, m), 7.14 and 7.62 (each 2H, each d, 8.7 Hz), 7.27-7.34 (2H, m).
IR (CH 2 Cl 2 3 ): 3428, 3026, 3015, 2925, 2870, 2666, 1739, 1708, 1643, 1613, 1594, 1526, 1499 / cm.
[Α] D = + 64.8 ° (MeOH, c = 1.02, 23 ° C).
No. 2a-184
CDCl 3 300 MHz
1.01 (1H, d, J = 10.2Hz), 1.18 and 1.26 (each 3H, each s), 1.55-2.50 (14H, m), 4.35 (1H, m), 5.35-5.55 (2H, m), 6.42 (1H, d, 8.7Hz), 7.46-7.52 (2H, m), 7.73 (1H, dd , J = 1.8 and 8.4 Hz), 7.83-7.89 (2H, m), 8.21 (1H, m), 8.59 (1H, d, J = 1.5 Hz) ,
IR (CH 2 Cl 2 3 ): 3451, 3031, 3014, 2925, 2870, 2660, 1739, 1708, 1650, 1604, 1513, 1463 / cm.
[Α] D = + 58.3 ° (MeOH, c = 1.00, 23 ° C).
No. 2a-185
CDCl 3 300 MHz
1.00 (1H, d, J = 10.2Hz), 1.18 and 1.25 (each 3H, each s), 1.55-2.50 (14H, m), 4.34 (1H, m), 5.35-5.54 (2H, m), 6.36 (1H, d, 8.7Hz), 7.37 (1H, t, J = 7.4Hz), 7.50 ( 1H, m), 7.57-7.59 (2H, m), 7.79 (1H, dd, J = 1.8 and 8.1 Hz), 7.99 (1H, d, J = 7, 8 Hz), 8.39 (1H, d, J = 1.8 Hz).
IR (CH 2 Cl 2 3 ): 3451, 3030, 3020, 2870, 2665, 1708, 1652, 1632, 1603, 1586, 1514, 1469, 1448 / cm.
[Α] D = + 59.4 ° (MeOH, c = 1.01, 24 ° C).
No. 2a-186
CDCl 3 300 MHz
1.00 (1H, d, J = 10.5 Hz), 1.17 and 1.25 (each 3H, each s), 1.54-2.50 (14H, m), 4.33 (1H, m), 5.35-5.54 (2H, m), 6.37 (1H, d, 8.7Hz), 7.37 (1H, t, J = 7.4Hz), 7.51 ( 1H, t, J = 7.8 Hz), 7.56 (1H, m), 7.70 (1H, dd, J = 1.2 and 8.4 Hz), 7.97 (3H, m).
IR (CH 2 Cl 2 3 ): 3451, 3030, 3014, 2924, 2870, 2671, 1739, 1708, 1652, 1577, 1517, 1488, 1471 / cm.
[Α] D = + 72.2 ° (MeOH, c = 1.00, 24 ° C).
No. 2a-187
CDCl 3 300 MHz
1.00 (1H, d, J = 9.8 Hz), 1.18 and 1.25 (each 3H, each s), 1.54-2.53 (14H, m), 4.07 (3H, s), 4.37 (1H, m), 5.30-5.54 (2H, m), 7.34 (1H, m), 7.47 (1H, s), 7.47-7.60 (2H, m), 7.93 (1H, d, J = 7.8Hz), 8.43 (1H, s), 8.49 (1H, d, J = 9.0Hz).
IR (CH 2 Cl 2 3 ): 3397, 3074, 3027, 3020, 3009, 2924, 1738, 1708, 1647, 1633, 1534, 1465, 1453 / cm.
[Α] D = + 43.7 ° (MeOH, c = 1.01, 25 ° C).
No. 2a-188
CDCl 3 300 MHz
0.97 (1H, d, J = 10.2Hz), 1.11 and 1.23 (each 3H, each s), 1.53-2.50 (14H, m), 4.23 (1H, m), 5.37-5.50 (2H, m), 8.10 (1H, d, J = 9.0 Hz), 6.20 (1H, m), 6.51 (1H, m), 6.97 (1H, m), 10.81 (1H, br).
IR (CH 2 Cl 2 3 ): 3450, 3236, 3112, 3029, 3015, 2925, 2871, 2645, 1701, 1616, 1558, 1516 / cm.
[Α] D = + 50.6 ° (MeOH, c = 1.01, 24 ° C).
No. 2a-189
CDCl 3 300 MHz
0.94 (1H, d, J = 9.9 Hz), 1.11 and 1.23 (each 3H, each s), 1.50-2.46 (14H, m), 3.93 (3H, s), 4.18 (1H, m), 5.35-5.52 (2H, m), 6.03 (1H, d, J = 9.3 Hz), 6.09 (1H, m), 6.48 (1H, m), 6.73 (1H, m).
IR (CH 2 Cl 2 3 ): 3452, 3102, 3028, 3007, 2925, 2871, 2666, 1739, 1708, 1650, 1536, 1499, 1471 / cm.
[Α] D = + 49.8 ° (MeOH, c = 1.01, 23 ° C).
M.p. 101.5-103.5 ° C.
No. 2a-190
CDCl 3 300 MHz
0.94 (1H, d, J = 10.2Hz), 1.11 and 1.21 (each 3H, each s), 1.54-2.47 (14H, m), 4.23 (1H, m), 5.33-5.52 (2H, m), 6.06 (1H, d, J = 9.0 Hz), 6.34 (1H, m), 6.75 (1H, m), 6.36 (1H, m), 9.71 (1H, br).
IR (CH 2 Cl 2 3 ): 3470, 3215, 3030, 3020, 3010, 2925, 2871, 2664, 1709, 1613, 1564, 1510 / cm.
[Α] D = + 43.3 ° (MeOH, c = 1.01, 24 ° C).
No. 2a-191
CDCl 3 300 MHz
0.96 (1H, d, J = 10.2 Hz), 1.11 and 1.22 (each 3H, each s), 1.55-2.44 (14H, m), 3.66 (3H, s), 4.20 (1H, m), 5.35-5.51 (2H, m), 5.93 (1H, d, J = 8.4Hz), 6.27 (1H, dd, J = 1.8 and 2.7 Hz), 6.56 (1H, t, J = 2.7 Hz), 7.19 (1H, t, J = 1.8 Hz).
IR (CH 2 Cl 2 3 ): 3452, 3031, 3018, 3006, 2925, 2871, 2662, 1736, 1710, 1634, 1609, 1556, 1498 / cm.
[Α] D = + 43.1 ° (MeOH, c = 1.01, 23 ° C).
No. 2a-192
CDCl 3 300 MHz
0.96 (1H, d, J = 10.5Hz), 1.11 and 1.21 (each 3H, each s), 1.43 (3H, t, J = 7.5Hz), 1.54 -2.44 (14H, m), 3.93 (2H, q, J = 7.5 Hz), 4.21 (1H, m), 5.33-5.51 (2H, m), 5, 94 (1H, d, J = 8.4 Hz), 6.27 (1H, dd, J = 1.8 and 2.7 Hz), 6.62 (1H, t, J = 2.7 Hz), 7.26 (1H, t, J = 1.8 Hz).
IR (CH 2 Cl 2 3 ): 3630, 3452, 3032, 3018, 3006, 2925, 2871, 2661, 1735, 1710, 1633, 1610, 1555, 1497 / cm.
[Α] D = + 40.1 ° (MeOH, c = 1.00, 23 ° C).
No. 2a-193
CDCl 3 300 MHz
0.95 (1H, d, J = 10.2Hz), 1.10 and 1.22 (each 3H, each s), 1.53-2.49 (14H, m), 2.58 (3H, s), 4.21 (1H, m), 5.35-5.54 (2H, m), 6.15 (1H, d, J = 8.1 Hz), 6.52 (1H, dd, J = 1.8 and 3.6 Hz), 7.29 (1H, t, J = 3.6 Hz), 7.94 (1H, t, J = 1.8 Hz).
IR (CH 2 Cl 2 3 ): 3516, 3450, 3410, 3152, 3027, 3015, 2925, 2871, 2670, 1732, 1648, 1574, 1509 / cm.
[Α] D = + 45.0 ° (MeOH, c = 1.01, 25 ° C).
No. 2a-194
CDCl 3 300 MHz
0.99 (1H, d, J = 10.2Hz), 1.11 and 1.24 (each 3H, each s), 1.52-2.53 (14H, m), 4.34 (1H, m), 5.33-5.57 (2H, m), 6.21 (1H, d, J = 8.6Hz), 7.35-7.50 (2H, m), 7.83 (1H , s), 7.86 (1H, m), 8.31 (1H, m).
IR (CH 2 Cl 2 3 ): 3443, 3067, 3013, 2925, 2870, 2665, 1708, 1651, 1515, 1493 / cm.
[Α] D = + 55.7 ° (MeOH, c = 1.01, 23 ° C).
No. 2a-195
CDCl 3 300 MHz
1.01 (1H, d, J = 10.0 Hz), 1.06 and 1.26 (each 3H, each s), 1.50-2.64 (14H, m), 2.68 (3H, s), 4.40 (1H, m), 5.36-5.61 (2H, m), 6.02 (1H, d, J = 9.4Hz), 7.30-7.42 (2H , m), 7.73-7.86 (2H, m).
IR (CH 2 Cl 2 3 ): 3510, 3434, 3062, 3029, 3014, 2924, 2871, 2669, 1708, 1650, 1563, 1539, 1500 / cm.
[Α] D = + 72.4 ° (MeOH, c = 1.00, 23 ° C).
Mp 111.0-112.0 ° C.
No. 2a-196
CDCl 3 300 MHz
0.42 and 1.04 (each 3H, each s), 0.80 (1H, d, J = 10.0 Hz), 1.11-2.48 (14H, m), 2.24 (3H, s), 4.02 (1H, m), 5.23-5.44 (2H, m), 5.53 (1H, d, J = 8.8Hz), 7.27-7.31 (2H , m), 7.42-7.48 (3H, m), 7.93 (1H, s).
IR (CH 2 Cl 2 3 ): 3419, 3114, 3025, 3006, 2924, 2871, 2662, 1737, 1709, 1636, 1540, 1519 / cm.
[Α] D = + 43.7 ° (MeOH, c = 1.01, 23 ° C).
No. 2a-197
CDCl 3 300 MHz
0.95 (1H, d, J = 10.0 Hz), 1.09 and 1.23 (each 3H, each s), 1.54-2.46 (18H, m), 2.77 (4H, br), 4.21 (1H, m), 5.32-5.54 (2H, m), 6.02 (1H, d, J = 8.6Hz), 7.43 (1H, s).
IR (CH 2 Cl 2 3 ): 3445, 3101, 3024, 3014, 2928, 2865, 2661, 1739, 1708, 1646, 1550, 1507 / cm.
[Α] D = + 51.9 ° (MeOH, c = 1.01, 23 ° C).
No. 2a-198
CDCl 3 300 MHz
0.96 (1H, d, J = 10.2 Hz), 1.11 and 1.22 (each 3H, each s), 1.50-2.44 (14H, m), 4.24 (1H, m), 4.42 (2H, s), 5.35-5.49 (2H, m), 6.25 (1H, d, J = 8.1 Hz), 7.33 (1H, m), 7.43 (1H, dd, J = 1.5 and 7.5 Hz), 7.49 (1H, d, J = 8.1 Hz), 7.60-7.63 (1H, m), 7 , 68 (1H, dd, J = 1.8 and 7.8 Hz), 8.02 (1H, d, J = 1.8 Hz), 8.19 (1H, dd, J = 1.5 and 8 , 1 Hz).
IR (CH 2 Cl 2 3 ): 3448, 3030, 3012, 2925, 2870, 1739, 1708, 1671, 1588, 1559, 1514, 1472 / cm.
[Α] D = + 56.9 ° (MeOH, c = 1.01, 24 ° C).
No. 2a-199
CDCl 3 300 MHz
0.96 (1H, d, J = 10.2 Hz), 1.11 and 1.22 (each 3H, each s), 1.51-2.46 (14H, m), 3.40 (1H, m), 3.76 (1H, m), 4.24 (1H, m), 5.33-5.51 (3H, m), 6.25 (1H, m), 7.16 (1H, m ), 7.24-7.33 (2H, m), 7.46 (1H, d, J = 7.5 Hz), 7.52-7.60 (2H, m), 7.85 (1H, dd, J = 1.8 and 4.5 Hz).
IR (CH 2 Cl 2 3 ): 3583, 3447, 3062, 3028, 3013, 2924, 2871, 2663, 1708, 1651, 1600, 1557, 1514, 1471 / cm.
[Α] D = + 54.8 ° (MeOH, c = 1.00, 23 ° C).
No. 2a-200
CDCl 3 300 MHz
0.96 (1H, d, J = 10.2 Hz), 1.12 and 1.23 (each 3H, each s), 1.51-2.46 (14H, m), 4.25 (1H, m), 5.34-5.51 (2H, m), 6.25 (1H, d, J = 8.4Hz), 7.02 and 7.10 (each 1H, each d, J = 12, 3 Hz), 7.23-7.33 (4H, m), 7.50 (1H, m), 7.64 (1H, dd, J = 1.8 and 7.8 Hz), 7.82 ( 1H, d, J = 1.8 Hz).
IR (CH 2 Cl 2 3 ): 3450, 3060, 3025, 3014, 2925, 2871, 2662, 1708, 1653, 1596, 1542, 1513, 1473 / cm.
[Α] D = + 62.5 ° (MeOH, c = 1.00, 24 ° C).
No. 2a-201
CDCl 3 300 MHz
0.95 (1H, d, J = 9.9 Hz), 1.15 and 1.22 (each 3H, each s), 1.55-2.60 (14H, m), 4.26 (1H, m), 5.35-5.63 (2H, m), 7.14 (1H, d, J = 9.9 Hz), 7.34 and 7.40 (each 1H, each d, J = 12, 9 Hz), 7.62-7.73 (4H, m), 8.25-8.30 (2H, m), 8.72 (1H, d, J = 1.5 Hz).
IR (CH 2 Cl 2 3 ): 3443, 3389, 3297, 3061, 3030, 3016, 2925, 2870, 1726, 1708, 1652, 1603, 1521, 1483, 1472, 1309 / cm.
[Α] D = + 61.1 ° (MeOH, c = 1.01, 23 ° C).
No. 2a-202
CDCl 3 300 MHz
0.96 (1H, d, J = 10.2 Hz), 1.09 and 1.22 (each 3H, each s), 1.52-2.43 (14H, m), 2.63 (3H, s), 4.25 (1H, m), 5.33-5.49 (2H, m), 6.19 (1H, d, J = 8.4Hz), 7.10 and 7.58 (each 2H, each d, J = 9.0 Hz), 7.21 (1H, m), 7.30-7.32 (2H, m), 7.46 (1H, d, J = 7.5 Hz) ,
IR (CH 2 Cl 2 3 ): 3511, 3453, 3062, 3032, 3014, 2925, 2870, 1739, 1708, 1650, 1595, 1556, 1516, 1482, 1471 / cm.
[Α] D = + 60.2 ° (MeOH, c = 1.01, 25 ° C).
No. 2a-203
CDCl 3 300 MHz
0.96 (1H, d, J = 10.5 Hz), 1.09 and 1.23 (each 3H, each s), 1.52-2.43 (14H, m), 4.23 (1H, m), 5.35-5.51 (2H, m), 5.93 (1H, d, 8.7 Hz), 6.56 (1H, dd, J = 0.9 and 1.8 Hz), 7.43 (1H, t, J = 1.8 Hz), 7.92 (1H, dd, J = 0.9 and 1.8 Hz).
IR (CH 2 Cl 2 3 ): 3517, 3450, 3134, 3031, 3008, 2925, 2870, 2667, 1708, 1656, 1588, 1570, 1514 / cm.
[Α] D = + 46.7 ° (MeOH, c = 0.92, 25 ° C).
No. 2b-1
[Α] D = + 25.6 ° (MeOH, c = 1.01, 23 ° C).
No. 2b-2
[Α] D = + 38.9 ° (MeOH, c = 1.01, 24 ° C).
No. 2c-1
[Α] D = + 60.5 ° (MeOH, c = 1.01, 22 ° C).
No. 2c-2
[Α] D = + 55.8 ° (MeOH, c = 0.92, 22 ° C).
No. 2c-3
[Α] D = + 54.7 ° (MeOH, c = 1.01, 22 ° C).
No. 2d-1
[Α] D = -6.2 ° (MeOH, c = 1.00, 21 ° C).
No. 2d-2
[Α] D = + 15.8 ° (MeOH, c = 0.34, 22 ° C).
No. 2d-3
[Α] D = + 31.6 ° (MeOH, c = 1.01, 22 ° C).
No. 2e-1
[Α] D = -9.4 ° (MeOH, c = 1.00, 22 ° C).
No. 2e-2
[Α] D = -1.8 ° (MeOH, c = 1.02, 23 ° C).
No. 2e-3
[Α] D = -6.7 ° (MeOH, c = 1.01, 23 ° C).
No. 2f-1
[Α] D = + 6.8 ° (MeOH, c = 1.01, 23 ° C).
No. 2f-2
[Α] D = -2.6 ° (MeOH, c = 1.00, 22 ° C).
No. 2f-3
[Α] D = -3.5 ° (MeOH, c = 1.01, 22 ° C).
No. 2g-1
[Α] D = + 54.6 ° (MeOH, c = 1.01, 24 ° C).

Die in den vorstehenden Beispielen hergestellten Verbindungen wurden für eine in vivo und in vitro Aktivität gemäß dem Verfahren, das in den nachstehenden experimentellen Beispielen gezeigt wird, getestet.The Compounds prepared in the preceding examples were for one in vivo and in vitro activity according to the method, which is shown in the experimental examples below tested.

Experiment 1 Bindung zum PGD2-RezeptorExperiment 1 Binding to the PGD 2 receptor

Material und VerfahrenMaterial and process

(1) Herstellung einer menschlichen Plättchenmembranfraktion(1) Preparation of a human platelet membrane fraction

Eine Blutprobe von Venen gesunder Freiwilliger (männliche und weibliche Erwachsene) wurde unter Verwendung einer Plastikspritze, die 3,8% Natriumcitrat enthielt, erhalten, in ein Plastik-Teströhrchen gegeben und sachte durch Inversion gemischt. Die Probe wurde dann bei 1800 U/min. 10 min. bei Raumtemperatur zentrifugiert, und der Überstand, der PRP (Plättchen-reiches Plasma) enthielt, wurde gesammelt. Das PRP wurde bei 2300 U/min. 22 min. bei Raumtemperatur rezentrifugiert, um die Plättchen zu erhalten. Die Plättchen wurden unter Verwendung eines Homogenisators (Ultra-Turrax) homogenisiert, gefolgt von einem 3-maligen Zentrifugieren bei 20.000 U/min. für 10 min. bei 4°C, um eine Plättchenmembranfraktion zu erhalten. Nach der Proteinbestimmung wurde die Membranfraktion auf 2 mg/ml eingestellt und in einem Eisschrank bei –80°C bis zur Verwendung konserviert.A Blood test of veins of healthy volunteers (male and female adults) was made using a plastic syringe containing 3.8% sodium citrate received, placed in a plastic test tube and gently Mixed inversion. The sample was then heated at 1800 rpm. 10 min. centrifuged at room temperature, and the supernatant, the PRP (platelet-rich Plasma) was collected. The PRP was at 2300 rpm. 22 min. recentrifuged at room temperature to add the platelets receive. The tiles were homogenized using a homogenizer (Ultra-Turrax), followed by centrifuging 3 times at 20,000 rpm. for 10 min. at 4 ° C, around a platelet membrane fraction to obtain. After protein determination, the membrane fraction became adjusted to 2 mg / ml and stored in a refrigerator at -80 ° C until use preserved.

(2) Bindung zu dem PGD2-Rezeptor(2) Binding to the PGD 2 receptor

Zu einer Bindungsreaktions-Lösung (50 mM Tris/HCl, pH 7,4, 5 mM MgCl2) (0,2 ml) wurden eine menschliche Plättchenmembranfraktion (0,1 mg) und 5 nM [3H]PGD2 (115 Ci/mmol) gegeben und bei 4°C für 90 min. umgesetzt. Nachdem die Umsetzung beendet war, wurde das Reaktionsgemisch durch ein Glasfaser-Filterpapier filtriert, mehrere Male mit gekühlter Kochsalzlösung gewaschen und eine Messung der auf dem Filterpapier zurückgehaltenen Radioaktivität durchgeführt. Die spezifische Bindung wurde durch Subtraktion der nicht spezifischen Bindung (der Bindung in Gegenwart von 10 μM PGD2) von der Gesamtbindung berechnet. Die Bindungsinhibitoraktivität jeder Verbindung wurde als Konzentration, die für 50% Inhibition (IC50) benötigt wird, ausgedrückt, welche durch Darstellen einer Substitutionskurve durch grafische Darstellung des Bindungsverhältnisses (Bindungsanteils) (%) in Gegenwart jeder Verbindung bestimmt wurde, wobei das Bindungsverhältnis (der Bindungsanteil) in Abwesenheit einer Testverbindung 100% beträgt. Die Ergebnisse werden in der nachstehenden Tabelle gezeigt.To a binding reaction solution (50 mM Tris / HCl, pH 7.4, 5 mM MgCl 2 ) (0.2 ml) was added a human platelet membrane fraction (0.1 mg) and 5 nM [ 3 H] PGD 2 (115 Ci / mmol) and at 4 ° C for 90 min. implemented. After the reaction was completed, the reaction mixture was filtered through a glass fiber filter paper, washed several times with cooled saline, and a measurement of the radioactivity retained on the filter paper was conducted. Specific binding was calculated by subtracting nonspecific binding (binding in the presence of 10 μM PGD 2 ) from total binding. The binding inhibitory activity of each compound was expressed as the concentration required for 50% inhibition (IC 50 ), which was determined by representing a substitution curve by plotting the binding ratio (binding ratio) (%) in the presence of each compound, wherein the binding ratio (the Binding fraction) in the absence of a test compound is 100%. The results are shown in the table below.

Figure 01040001
Figure 01040001

Experiment 2 Evaluierung der antagonistischen Aktivität gegenüber dem PGD2-Rezeptor unter Verwendung menschlicher BlutplättchenExperiment 2 Evaluation of antagonistic activity against the PGD 2 receptor using human platelets

Periphäres Blut wurde von einem gesunden Freiwilligen unter Verwendung einer Spritze erhalten, in welche zuvor 1/9 des Spritzenvolumens einer Zitronensäure/Dextroselösung gegeben worden war. Die Spritze wurde für 10 min. einem Zentrifugieren bei 180 g unterworfen, um den Überstand (PRP: Plättchen-reiches Plasma) zu erhalten. Das resultierende RRP wurde dreimal mit einem Waschpuffer gewaschen, und die Anzahl der Plättchen wurde mit einem Mikrozellzähler gezählt. Eine Suspension, eingestellt, um Plättchen mit einer Endkonzentration von 5 × 108/ml zu enthalten, wurde auf 37°C erwärmt, und dann für 5 min. der Vorbehandlung mit 3-Isobutyl-1-methylxanthin (0,5 mM) unterworfen. Zu der Suspension wurde eine auf verschiedene Konzentrationen verdünnte Testverbindung gegeben. Zehn Minuten später wurde die Umsetzung durch die Zugabe von 0,1–2,0 μM PGD2 induziert und 15 Minuten später durch die Zugabe von HCl gestoppt. Die Plättchen wurden mit einem Ultraschall-Homogenisator zerstört. Nach dem Zentrifugieren wurde das cAMP in dem Überstand durch Radioassay bestimmt. PGD2-Rezeptorantagonismus eines Arzneistoffs wurde wie folgt ausgewertet. Die Inhibitionsrate hinsichtlich cAMP, die durch die Zugabe von PGD2 zunimmt, wurde bei einer einzelnen Konzentration bestimmt, und dann wurde die Konzentration des Arzneistoffs, der für 50% Inhibition (IC50) benötigt wurde, berechnet. Die Ergebnisse werden in der nachstehenden Tabelle gezeigt.Peripheral blood was obtained from a healthy volunteer using a syringe into which had previously been added 1/9 of the syringe volume of a citric acid / dextrose solution. The syringe was for 10 min. centrifuged at 180 g to obtain the supernatant (PRP: platelet-rich plasma). The resulting RRP was washed three times with a washing buffer and the number of platelets was counted with a microcell counter. A suspension adjusted to contain platelets at a final concentration of 5 x 10 8 / ml was warmed to 37 ° C, and then for 5 min. pretreatment with 3-isobutyl-1-methylxanthine (0.5 mM). To the suspension was added a test compound diluted to various concentrations. Ten minutes later, the reaction was induced by the addition of 0.1-2.0 μM PGD 2 and stopped 15 minutes later by the addition of HCl. The slides were destroyed with an ultrasonic homogenizer. After centrifugation, the cAMP in the supernatant was determined by radioassay. PGD 2 receptor antagonism of a drug was evaluated as follows. The rate of inhibition of cAMP, which increases with the addition of PGD 2 , was determined at a single concentration and then the concentration of drug required for 50% inhibition (IC 50 ) was calculated. The results are shown in the table below.

Figure 01050001
Figure 01050001

Experiment 3 Experiment unter Verwendung des NasenokklusionsmodellsExperiment 3 experiment using the nasal occlusion model

Das zur Messung des Widerstands in der Nasenhöhle verwendete Verfahren und die Bewertung der anti-Nasenokklusion unter Verwendung eines Meerschweinchens werden nachstehend beschrieben.The Method used to measure resistance in the nasal cavity; and the evaluation of anti-nasal occlusion using a guinea pig are described below.

Eine 1%-ige Ovalbuminlösung (OVA) wurde mit einem Ultraschall-Vernebler behandelt, um ein Aerosol zu erhalten. Ein männliches Hartley-Meerschweinchen wurde durch zweimaliges Inhalieren des Aerosols für 10 min. in einwöchigen Interwallen sensibilisiert. Sieben Tage nach der Sensibilisierung wurde das Meerschweinchen einem Antigen ausgesetzt, um die Reaktion zu initiieren. Dann wurde die Luftröhre unter Anästhesie mit Pentobarbital (30 mg/kg, i.p.) eingeschnitten, und Kanülen wurden in die Luftröhre an den Lungen- und Nasenhöhlenseiten insertiert. Die Röhre, die an der Lungenseite insertiert war, wurde mit einem künstlichen Beatmungsgerät verbunden, das 4 ml Luft 60-mal/min. lieferte. Nach Blockierung der spontanen Atmung eines Meerschweinchens mit Garamin (2 mg/kg, i.v.) wurde mit einem künstlichen Beatmungsgerät mit der Frequenz von 70-mal/min. und der Flussrate von 4 ml Luft/Zeit Luft der Schnauzenseite zugeführt, und der für die Sauerstoffsättigung benötigte Atmosphärendruck wurde unter Verwendung eines an der Zweigstelle eingebauten Messwandlers gemessen. Die Messung wurde als ein Parameter des Widerstands in der Nasenhöhle verwendet. Das Einwirken eines Antigens wurde durch Aerosolerzeugung aus einer 3% OVA-Lösung für 3 min. zwischen dem Beatmungsgerät und der Nasenhöhlenkanüle durchgeführt. Der Testarzneistoff wurde 10 min. vor dem Einwirken des Antigens intravenös injiziert. Der Widerstand in der Nase wurde zwischen 0 bis 30 min. kontinuierlich gemessen, und die Wirkung wurde als Inhibitionsrate zu der, die für das Vehikel erhalten wurde, unter Verwendung der AUC für 30 min. (auf der vertikalen Achse: Widerstand in der Nasenhöhle (cm H2O) und auf der horizontalen Achse: Zeit (0–30 min)) als eine Indikation ausgedrückt. Das Ergebnis wird nachstehend gezeigt.A 1% ovalbumin solution (OVA) was treated with an ultrasonic nebulizer to obtain an aerosol. A male Hartley guinea pig was injected by inhaling the aerosol twice for 10 min. Sensitized in one-week intervals. Seven days after sensitization, the guinea pig was exposed to an antigen to initiate the reaction. The trachea was then incised under anesthesia with pentobarbital (30 mg / kg, ip) and cannulas were inserted into the trachea at the pulmonary and nasal cavity sides. The tube, which was inserted at the lung side, was connected to an artificial respirator, which received 4 ml of air 60 times / min. provided. After blocking the spontaneous respiration of a guinea pig with garamine (2 mg / kg, iv) was treated with an artificial respirator with the frequency of 70 times / min. and the flow rate of 4 ml of air / time was supplied to the snout-side air, and the atmospheric pressure required for the oxygen saturation was measured using a branch-mounted transducer. The measurement was used as a parameter of resistance in the nasal cavity. The action of an antigen was determined by aerosol generation from a 3% OVA solution for 3 min. between the ventilator and the nasal cannula. The test drug was 10 min. injected intravenously before exposure to the antigen. The resistance in the nose was between 0 to 30 min. was measured continuously and the effect was measured as the inhibition rate to that obtained for the vehicle using the AUC for 30 min. (on the vertical axis: resistance in the nasal cavity (cm H 2 O) and on the horizontal axis: time (0-30 min)) expressed as one indication. The result is shown below.

Figure 01060001
Figure 01060001

Formulierung 1 Herstellung der TablettenFormulation 1 Preparation of the tablets

Die Tabletten, wobei jede 40 mg des Wirkstoffs enthielt, wurden auf herkömmliche Weise hergestellt.The Tablets, each containing 40 mg of the active ingredient, were added conventional Made way.

Claims (10)

Verbindung der Formel (Ib):
Figure 01070001
steht, wobei A Alkylen ist, das gegebenenfalls durch ein Heteroatom oder Phenylen unterbrochen sein kann, eine Oxogruppe enthält und/oder eine ungesättigte Bindung aufweist; B Wasserstoff, Alkyl, Aralkyl oder Acyl ist; R für COOR1, CH2OR2 oder CON(R3)R4 steht; R1 Wasserstoff oder Alkyl ist; R2 Wasserstoff oder Alkyl ist; R3 und R4 jeweils unabhängig Wasserstoff, Alkyl, Hydroxy oder Alkylsulfonyl sind; X1 eine Einfachbindung, Phenylen, Naphthylen, Thiophendiyl, Indoldiyl oder Oxazoldiyl ist; X2 eine Einfachbindung, -N=N-, -N=CH-, -CH=N-, -CH=N-N-, -CH=N-O-, -C=NNHCSNH-, -C=NNHCONH-, -CH=CH-, -CH(OH)-, -C(Cl)=C(Cl)-, -(CH2)n-, Ethinylen, -N(R5)-, -N(R51)CO-, -N(R52)SO2-, -N(R53)CON(R54)-, -CON(R55)-, -SO2N(R56)-, -O-, -S-, -SO-, -SO2-, -CO-, Oxadiazoldiyl, Thiadiazoldiyl oder Tetrazoldiyl ist; X3 Alkyl, Alkenyl, Alkinyl, Aryl, Aralkyl, ein heterocyclischer Rest, Cycloalkyl, Cycloalkenyl, Thiazolinylidenmethyl, Thiazolidinylidenmethyl, -CH=NR6 oder -N=C(R7)R8 ist; R5, R51, R52, R53, R54, R55 und R56 jeweils Wasserstoff oder Alkyl sind; R6 Wasserstoff, Alkyl, Hydroxy, Alkoxy, Carbamoyloxy, Thiocarbamoyloxy, Ureido oder Thioureido ist; R7 und R8 jeweils unabhängig Alkyl, Alkoxy oder Aryl sind; und n gleich 1 oder 2 ist; wobei ein cyclischer Substituent 1 bis 3 Substituenten, ausgewählt aus Nitro, Alkoxy, Sulfamoyl, substituiertem oder unsubstituiertem Amino, Acyl, Acyloxy, Hydroxy, Halogen, Alkyl, Alkinyl, Carboxy, Alkoxycarbonyl, Aralkoxycarbonyl, Aryloxycarbonyl, Mesyloxy, Cyano, Alkenyloxy, Hydroxyalkyl, Trifluormethyl, Alkylthio, -N=PPh3, Oxo, Thioxo, Hydroxyimino, Alkoxyimino, Phenyl und Alkylendioxy oder deren Salzen oder Hydraten davon, aufweisen kann; mit der Maßgabe, dass die Verbindungen (a), wobei X1 und X2 Einfachbindungen sind und X3 Phenyl ist; (b), wobei X1 eine Einfachbindung ist, X2 für -O- steht und X3 Benzyl ist;
Figure 01080001
ausgenommen sind.Compound of the formula (Ib):
Figure 01070001
wherein A is alkylene, which may optionally be interrupted by a heteroatom or phenylene, contains an oxo group and / or has an unsaturated bond; B is hydrogen, alkyl, aralkyl or acyl; R is COOR 1 , CH 2 OR 2 or CON (R 3 ) R 4 ; R 1 is hydrogen or alkyl; R 2 is hydrogen or alkyl; R 3 and R 4 are each independently hydrogen, alkyl, hydroxy or alkylsulfonyl; X 1 is a single bond, phenylene, naphthylene, thiophenediyl, indolediyl or oxazolediyl; X 2 is a single bond, -N = N-, -N = CH-, -CH = N-, -CH = NN-, -CH = NO-, -C = NNHCSNH-, -C = NNHCONH-, -CH = CH, -CH (OH) -, -C (Cl) CC (Cl) -, - (CH 2 ) n -, ethynylene, -N (R 5 ) -, -N (R 51 ) CO-, - N (R 52) SO 2 -, -N (R 53) CON (R 54) -, -CON (R 55) -, -SO 2 N (R 56) -, -O-, -S-, -SO Is -SO 2 -, -CO-, oxadiazolediyl, thiadiazolediyl or tetrazolediyl; X 3 is alkyl, alkenyl, alkynyl, aryl, aralkyl, heterocyclic, cycloalkyl, cycloalkenyl, thiazolinylidenemethyl, thiazolidinylidenemethyl, -CH = NR 6 or -N = C (R 7 ) R 8 ; R 5 , R 51 , R 52 , R 53 , R 54 , R 55 and R 56 are each hydrogen or alkyl; R 6 is hydrogen, alkyl, hydroxy, alkoxy, carbamoyloxy, thiocarbamoyloxy, ureido or thioureido; R 7 and R 8 are each independently alkyl, alkoxy or aryl; and n is 1 or 2; wherein a cyclic substituent has 1 to 3 substituents selected from nitro, alkoxy, sulfamoyl, substituted or unsubstituted amino, acyl, acyloxy, hydroxy, halogen, alkyl, alkynyl, carboxy, alkoxycarbonyl, aralkoxycarbonyl, aryloxycarbonyl, mesyloxy, cyano, alkenyloxy, hydroxyalkyl, Trifluoromethyl, alkylthio, -N = PPh 3 , oxo, thioxo, hydroxyimino, alkoxyimino, phenyl and alkylenedioxy or their salts or hydrates thereof; with the proviso that the compounds are (a) wherein X 1 and X 2 are single bonds and X 3 is phenyl; (b) wherein X 1 is a single bond, X 2 is -O- and X 3 is benzyl;
Figure 01080001
with exception of. Verbindung nach Anspruch 1, ein Salz oder Hydrat davon, wobei
Figure 01090001
steht.A compound according to claim 1, a salt or hydrate thereof, wherein
Figure 01090001
stands. Verbindung nach Anspruch 2, ein Salz oder Hydrat davon, wobei R für COOR1 steht.A compound according to claim 2, a salt or hydrate thereof, wherein R is COOR 1 . Verbindung nach Anspruch 2, ein Salz oder Hydrat davon, wobei X1 Phenylen oder Thiophendiyl ist, X2 eine Einfachbindung, -N=N-, -CH=CH-, Ethinylen, -O-, -S-, -CO-, -CON(R55)-, -N(R51)CO- ist und X3 Phenyl oder Thienyl ist.A compound according to claim 2, a salt or hydrate thereof, wherein X 1 is phenylene or thiophenediyl, X 2 is a single bond, -N = N-, -CH = CH-, ethynylene, -O-, -S-, -CO-, -CON (R 55 ) -, -N (R 51 ) CO- and X 3 is phenyl or thienyl. Verbindung nach Anspruch 1, ein Salz oder Hydrat davon, wobei
Figure 01090002
steht.A compound according to claim 1, a salt or hydrate thereof, wherein
Figure 01090002
stands. Verbindung nach Anspruch 5, ein Salz oder Hydrat davon, wobei B Wasserstoff ist, X1 und X2 beide eine Einfachbindung sind, X3 Thienyl, Thiazolyl, Thiadiazolyl, Isothiazolyl, Pyrrolyl, Pyridyl, Benzofuryl, Benzimidazolyl, Benzothienyl, Dibenzofuryl, Dibenzothienyl, Chinolyl oder Indolyl ist.A compound according to claim 5, a salt or hydrate thereof, wherein B is hydrogen, X 1 and X 2 are both a single bond, X 3 is thienyl, thiazolyl, thiadiazolyl, isothiazolyl, pyrrolyl, pyridyl, benzofuryl, benzimidazolyl, benzothienyl, dibenzofuryl, dibenzothienyl, Quinolyl or indolyl is. Verbindung nach Anspruch 5, ein Salz oder Hydrat davon, wobei X1 Phenylen, Thiophendiyl, Indoldiyl oder Oxazoldiyl ist, X2 eine Einfachbindung, -N=N-, -CH=CH-, Ethinylen, -S- oder -O- ist und X3 Aryl oder ein heterocyclischer Rest ist.A compound according to claim 5, a salt or hydrate thereof, wherein X 1 is phenylene, thiophenediyl, indolediyl or oxazolediyl, X 2 is a single bond, -N = N-, -CH = CH-, ethynylene, -S- or -O- and X 3 is aryl or a heterocyclic radical. Verbindung der nachstehenden Formel (Ib), zur Verwendung in einem Verfahren zur Behandlung von Krankheiten, die eine Fehlfunktion der Mastzellen einschließen, trachealer Kontraktion, Asthma, allergischer Rhinitis, allergischer Konjunktivitis, Urtikaria, Verletzungen aufgrund von Ischämie-Reperfusion, Nasenokklusion und Entzündung:
Figure 01100001
steht; wobei A Alkylen ist, das gegebenenfalls durch ein Heteroatom oder Phenylen unterbrochen sein kann, eine Oxogruppe enthält und/oder eine ungesättigte Bindung aufweist; B Wasserstoff, Alkyl, Aralkyl oder Acyl ist; R für COOR1, CH2OR2 oder CON(R3)R4 steht; R1 Wasserstoff oder Alkyl ist; R2 Wasserstoff oder Alkyl ist; R3 und R4 jeweils unabhängig Wasserstoff, Alkyl, Hydroxy oder Alkylsulfonyl sind; X1 eine Einfachbindung, Phenylen, Naphthylen, Thiophendiyl, Indoldiyl oder Oxazoldiyl ist; X2 eine Einfachbindung, -N=N-, -N=CH-, -CH=N-, -CH=N-N-, -CH=N-O-, -C=NNHCSNH-, -C=NNHCONH-, -CH=CH-, -CH(OH)-, -C(Cl)=C(Cl)-, -(CH2)n-, Ethinylen, -N(R5)-, -N(R51)CO-, -N(R52)SO2-, -N(R53)CON(R54)-, -CON(R55)-, -SO2N(R56)-, -O-, -S-, -SO-, -SO2-, -CO-, Oxadiazoldiyl, Thiadiazoldiyl oder Tetrazoldiyl ist; X3 Alkyl, Alkenyl, Alkinyl, Aryl, Aralkyl, ein heterocyclischer Rest, Cycloalkyl, Cycloalkenyl, Thiazolinylidenmethyl, Thiazolidinylidenmethyl, -CH=NR6 oder -N=C(R7)R8 ist; R5, R51, R52, R53, R54, R55 und R56 jeweils Wasserstoff oder Alkyl sind; R6 Wasserstoff, Alkyl, Hydroxy, Alkoxy, Carbamoyloxy, Thiocarbamoyloxy, Ureido oder Thioureido ist; R7 und R8 jeweils unabhängig Alkyl, Alkoxy oder Aryl sind; und n gleich 1 oder 2 ist; wobei ein cyclischer Substituent 1 bis 3 Substituenten, ausgewählt aus Nitro, Alkoxy, Sulfamoyl, substituiertem oder unsubstituiertem Amino, Acyl, Acyloxy, Hydroxy, Halogen, Alkyl, Alkinyl, Carboxy, Alkoxycarbonyl, Aralkoxycarbonyl, Aryloxycarbonyl, Mesyloxy, Cyano, Alkenyloxy, Hydroxyalkyl, Trifluormethyl, Alkylthio, -N=PPh3, Oxo, Thioxo, Hydroxyimino, Alkoxyimino, Phenyl und Alkylendioxy oder deren Salzen oder Hydraten davon, aufweisen kann; mit der Maßgabe, dass die Verbindungen (a), wobei X1 und X2 Einfachbindungen sind und X3 Phenyl ist; und (b), wobei X1 eine Einfachbindung ist, X2 für -O- steht und X3 Benzyl ist, ausgenommen sind.A compound of the following formula (Ib) for use in a method of treating diseases involving mast cell dysfunction, tracheal contraction, asthma, allergic rhinitis, allergic conjunctivitis, urticaria, ischemia-reperfusion injury, nasal occlusion, and inflammation:
Figure 01100001
stands; wherein A is alkylene, which may optionally be interrupted by a heteroatom or phenylene, contains an oxo group and / or has an unsaturated bond; B is hydrogen, alkyl, aralkyl or acyl; R is COOR 1 , CH 2 OR 2 or CON (R 3 ) R 4 ; R 1 is hydrogen or alkyl; R 2 is hydrogen or alkyl; R 3 and R 4 are each independently hydrogen, alkyl, hydroxy or alkylsulfonyl; X 1 is a single bond, phenylene, naphthylene, thiophenediyl, indolediyl or oxazolediyl; X 2 is a single bond, -N = N-, -N = CH-, -CH = N-, -CH = NN-, -CH = NO-, -C = NNHCSNH-, -C = NNHCONH-, -CH = CH, -CH (OH) -, -C (Cl) CC (Cl) -, - (CH 2 ) n -, ethynylene, -N (R 5 ) -, -N (R 51 ) CO-, - N (R 52) SO 2 -, -N (R 53) CON (R 54) -, -CON (R 55) -, -SO 2 N (R 56) -, -O-, -S-, -SO Is -SO 2 -, -CO-, oxadiazolediyl, thiadiazolediyl or tetrazolediyl; X 3 is alkyl, alkenyl, alkynyl, aryl, aralkyl, heterocyclic, cycloalkyl, cycloalkenyl, thiazolinylidenemethyl, thiazolidinylidenemethyl, -CH = NR 6 or -N = C (R 7 ) R 8 ; R 5 , R 51 , R 52 , R 53 , R 54 , R 55 and R 56 are each hydrogen or alkyl; R 6 is hydrogen, alkyl, hydroxy, alkoxy, carbamoyloxy, thiocarbamoyloxy, ureido or thioureido; R 7 and R 8 are each independently alkyl, alkoxy or aryl; and n is 1 or 2; wherein a cyclic substituent has 1 to 3 substituents selected from nitro, alkoxy, sulfamoyl, substituted or unsubstituted amino, acyl, acyloxy, hydroxy, halogen, alkyl, alkynyl, carboxy, alkoxycarbonyl, aralkoxycarbonyl, aryloxycarbonyl, mesyloxy, cyano, alkenyloxy, hydroxyalkyl, Trifluoromethyl, alkylthio, -N = PPh 3 , oxo, thioxo, hydroxyimino, alkoxyimino, phenyl and alkylenedioxy or their salts or hydrates thereof; with the proviso that the compounds are (a) wherein X 1 and X 2 are single bonds and X 3 is phenyl; and (b) wherein X 1 is a single bond, X 2 is -O- and X 3 is benzyl, except. Verwendung eines PGD2-Antagonisten, umfassend eine Verbindung der Formel (Ib) wie in Anspruch 8 definiert oder ein Salz oder Hydrat davon als wirksamen Bestandteil bei der Herstellung eines Arzneimittels zur Behandlung von Krankheiten, die eine Fehlfunktion der Mastzellen einschließen, trachealer Kontraktion, Asthma, allergischer Rhinitis, allergischer Konjunktivitis, Urtikaria, Verletzungen aufgrund von Ischämie-Reperfusion, Nasenokklusion und Entzündung.Use of a PGD 2 antagonist comprising a compound of formula (Ib) as defined in claim 8 or a salt or hydrate thereof as an effective ingredient in the manufacture of a medicament for the treatment of diseases involving mast cell dysfunction, tracheal contraction, asthma , allergic rhinitis, allergic conjunctivitis, urticaria, injuries due to ischemia-reperfusion, nasal occlusion and inflammation. Verwendung eines PGD2-Antagonisten, umfassend eine Verbindung der Formel (Ib) wie in Anspruch 9 definiert oder ein Salz oder Hydrat davon als wirksamen Bestandteil bei der Herstellung eines Arzneimittels zur Behandlung von Krankheiten, die eine Fehlfunktion der Mastzellen einschließen, trachealer Kontraktion, Asthma, allergischer Rhinitis, allergischer Konjunktivitis, Urtikaria, Verletzungen aufgrund von Ischämie-Reperfusion, Nasenokklusion und Entzündung.Use of a PGD 2 antagonist comprising a compound of formula (Ib) as defined in claim 9 or a salt or hydrate thereof as an effective ingredient in the manufacture of a medicament for the treatment of diseases involving mast cell dysfunction, tracheal contraction, asthma , allergic rhinitis, allergic conjunctivitis, urticaria, injuries due to ischemia-reperfusion, nasal occlusion and inflammation.
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TW513422B (en) 2002-12-11
AU6137096A (en) 1997-01-22
PT837052E (en) 2006-12-29
BR9608498B1 (en) 2008-11-18
DK0837052T3 (en) 2007-01-02
US6498190B1 (en) 2002-12-24
IL122332A0 (en) 1998-04-05
KR100428601B1 (en) 2004-09-16
BR9608498A (en) 1999-07-06
EA199800074A1 (en) 1998-08-27
ES2270438T3 (en) 2007-04-01
ATE337294T1 (en) 2006-09-15
JP3195361B2 (en) 2001-08-06
US6384075B1 (en) 2002-05-07
US6172113B1 (en) 2001-01-09
CN1193315A (en) 1998-09-16
WO1997000853A1 (en) 1997-01-09
TR199701667T2 (en) 1999-10-21
IS4623A (en) 1997-11-28

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